Papers - Chida, Noritaka

Development of a Chiral N -Alkoxyamide Strategy and Application to the Asymmetric Total Synthesis of Fasicularin

Minamikawa R., Fukaya K., Kobayashi A., Komiya Y., Yamamoto S., Urabe D., Chida N., Sato T.

Synthesis (Germany) (Synthesis (Germany))  53 ( 24 ) 4621 - 4635 2021.12

ISSN  00397881

　View Summary

The asymmetric total synthesis of fasicularin by a chiral Nalkoxyamide strategy is reported. Incorporation of the chiral alkoxy group onto an amide nitrogen changes the original reactivity of the amide, enabling two key transformations: aza-spirocyclization and the reductive Strecker reaction. DFT calculations indicate that pyramidalization of the N-alkoxyamide nitrogen is crucial to produce a cyclic hemiaminal in equilibrium, which undergoes aza-spirocyclization. The chiral alkoxy group is also used as a stereocontrol element to establish two consecutive stereocenters. The iridium-catalyzed reductive Strecker reaction of the N-alkoxylactam provides the aminonitrile with high diastereoselectivity.

• Access to Document (DOI)

Total Synthesis of Skipped Diene Natural Products

Sato T., Suto T., Nagashima Y., Mukai S., Chida N.

Asian Journal of Organic Chemistry (Asian Journal of Organic Chemistry)  10 ( 10 ) 2486 - 2502 2021.10

ISSN  21935807

　View Summary

Skipped dienes (1,4-dienes) are widely distributed in a variety of biologically active natural products. The synthesis of these skipped dienes is a relatively undeveloped area compared with that of conjugated dienes (1,3-dienes) due to the sp3-hybridized carbon between two olefins. Especially, development of methods to meet both high stereoselectivity and convergency is highly challenging. This review focuses on recent advances in the synthesis of skipped dienes in the total synthesis of complex natural products, which are classified into three classes; a) skipped dienes comprised of two disubstituted olefins, b) skipped dienes including trisubstituted olefin(s), and c) 3-methyl skipped dienes.

• Access to Document (DOI)

Five-Step Total Synthesis of (±)-Aspidospermidine by a Lactam Strategy via an Azomethine Ylide

Katahara S., Sugiyama Y., Yamane M., Komiya Y., Sato T., Chida N.

Organic Letters (Organic Letters)  23 ( 8 ) 3058 - 3063 2021.04

ISSN  15237060

　View Summary

A five-step total synthesis of (±)-aspidospermidine (1) based on a lactam strategy is reported. Our synthesis features an iridium-catalyzed reductive Michael addition/[3+2] cycloaddition cascade to give a tricyclic ketone intermediate from a simple lactam via an azomethine ylide. The developed strategy enables easily available lactams to be used as stable surrogates of multisubstituted amines and would be applicable to a unified total synthesis of complex Aspidosperma alkaloids.

• Access to Document (DOI)

Identification of madangamine A as a novel lysosomotropic agent to inhibit autophagy

Miura K., Kawano S., Suto T., Sato T., Chida N., Simizu S.

Bioorganic and Medicinal Chemistry (Bioorganic and Medicinal Chemistry)  34 2021.03

ISSN  09680896

　View Summary

Madangamines are marine natural products isolated from Xestospongia ingens, and madangamine A–E with a different D-ring structure have been reported. We have reported that madangamine A has strong anti-proliferative activity against various human cancer cell lines. In this study, to clarify the anti-proliferative activity of madangamine A, we searched for molecular target of the madangamine A in human cells. Treatment with madangamine A increased the levels of LC3-II and p62, autophagy-related proteins, concomitant with growth inhibition. Moreover, madangamine A resulted in lysosome enlargement and increase in lysosomal pH, which are same phenomena observed in chloroquine-treated cells. These results suggest that madangamine A is a novel lysosome inhibitor, and the anti-proliferative activity of madangamine A is due to the inhibition of lysosome function.

• Access to Document (DOI)

Seven-Step Synthesis of All-Nitrogenated Sugar Derivatives Using Sequential Overman Rearrangements

Okuyama Y., Kidena M., Kato E., Kawano S., Ishii K., Maie K., Miura K., Simizu S., Sato T., Chida N.

Angewandte Chemie - International Edition (Angewandte Chemie - International Edition)  60 ( 10 ) 5193 - 5198 2021.03

ISSN  14337851

　View Summary

All-nitrogenated sugars (ANSs), in which all hydroxy groups in a carbohydrate are replaced with amino groups, are anticipated to be privileged structures with useful biological activities. However, ANS synthesis has been challenging due to the difficulty in the installation of multi-amino groups. We report herein the development of a concise synthetic route to peracetylated ANSs in seven steps from commercially available monosaccharides. The key to success is the use of the sequential Overman rearrangement, which enables formal simultaneous substitution of four or five hydroxy groups in monosaccharides with amino groups. A variety of ANSs are available through the same reaction sequence starting from different initial monosaccharides by chirality transfer of secondary alcohols. Transformations of the resulting peracetylated ANSs such as glycosylation and deacetylation are also demonstrated. Biological studies reveal that ANS-modified cholesterol show cytotoxicity against human cancer cell lines, whereas each ANS and cholesterol have no cytotoxicity.

• Access to Document (DOI)

Unified Total Synthesis of Pentacyclic Stemoamide-type Alkaloids

Soda Y., Sugiyama Y., Yoritate M., Tajima H., Shibuya K., Ogihara C., Oishi T., Sato T., Chida N.

Organic Letters (Organic Letters)  22 ( 19 ) 7502 - 7507 2020.10

ISSN  15237060

　View Summary

The collective synthesis of pentacyclic stemoamide-type alkaloids is recognized as a daunting task despite high demand for a comprehensive biological profiling of these natural products. In this Letter, we report a unified synthesis of seven pentacyclic alkaloids and two unnatural derivatives. The keys to success are (1) the chemoselective assembly of four five-membered building blocks, (2) the direct oxidation of pyrrolidine natural products to pyrrole derivatives, and (3) the stereodivergent construction of totally E- or Z-substituted butenolides.

• Access to Document (DOI)

Copper-Catalyzed Electrophilic Etherification of Arylboronic Esters with Isoxazolidines

Katahara S., Takahashi T., Nomura K., Uchiyama M., Sato T., Chida N.

Chemistry - An Asian Journal (Chemistry - An Asian Journal)  15 ( 12 ) 1869 - 1872 2020.06

ISSN  18614728

　View Summary

A copper-catalyzed electrophilic etherification of arylboronic esters is reported. Isoxazolidines are utilized as easily available and stable [RO]+ surrogates to give 1,3-amino aryl ethers. The O-selective arylation of isoxazolidines takes place without causing competitive N-arylation. In contrast to previously reported anionic conditions, our copper-catalyzed conditions are mild enough to achieve high functional group tolerance. Preliminary mechanistic studies and DFT calculations support that the reaction proceeds via a transmetalation/oxidative addition pathway, followed by a Lewis acid-promoted reductive elimination to induce the crucial O-selectivity.

• Access to Document (DOI)

Synthesis of Saxitoxin and Its Derivatives

Okuyama Y., Okamoto R., Mukai S., Kinoshita K., Sato T., Chida N.

Organic Letters (Organic Letters)   2020

ISSN  15237060

　View Summary

The chiral synthesis of (+)-saxitoxin and its derivatives is described. Two consecutive carbon-nitrogen bonds at C-5 and C-6 in saxitoxin were effectively installed by the sequential Overman rearrangement of an allylic vicinal diol derived from d-malic acid. The bicyclic guanidine unit was constructed by the intramolecular aminal formation of an acyclic bis-guanidine derivative possessing a ketone carbonyl at C-4. From the bicyclic aminal intermediate, (+)-saxitoxin, (+)-decarbamoyl-β-saxitoxinol [(+)-dc-β-saxitoxinol], and the unnatural skeletal isomer, (-)-iso-dc-saxitoxinol, were synthesized.

• Access to Document (DOI)

Copper-Catalyzed Electrophilic Amidation of Organotrifluoroborates with Use of N-Methoxyamides

Banjo S., Nakasuji E., Meguro T., Sato T., Chida N.

Chemistry - A European Journal (Chemistry - A European Journal)  25 ( 33 ) 7941 - 7947 2019.06

ISSN  09476539

　View Summary

© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim A copper-catalyzed electrophilic amidation of aryltrifluoroborates with use of N-methoxyamides is reported. The reaction shows high functional group compatibility derived from two distinct features: 1) the high stability of the N-methoxyamides and 2) the nonbasic mild conditions in the presence of LiCl. The developed method can also be applied to the synthesis of enamides, which are widely distributed in natural products. Preliminary mechanistic studies suggest that the initial step is the transmetalation of the aryltrifluoroborate by the assistance of LiCl, and the resulting aryl copper intermediate provides the anilide through non-SN2 oxidative addition to the N-methoxyamide and subsequent reductive elimination.

• Access to Document (DOI)

Approach to Fully Substituted Cyclic Nitrones from N-Hydroxylactam Derivatives: Development and Application to the Total Synthesis of Cylindricine C

Hiraoka S., Matsumoto T., Matsuzaka K., Sato T., Chida N.

Angewandte Chemie - International Edition (Angewandte Chemie - International Edition)  58 ( 13 ) 4381 - 4385 2019.03

ISSN  14337851

　View Summary

© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim An approach to cyclic nitrones from N-hydroxylactam derivatives is documented. The nucleophilic addition of an organolithium reagent to an N-OSEM [SEM=2-(trimethylsilyl)ethoxymethyl] lactam forms a five-membered chelated intermediate, which undergoes both elimination and deprotection to give a fully substituted nitrone in a one-pot process. When combined with the N-oxidation of easily available chiral lactams, this method becomes especially useful for the quick synthesis of chiral nitrones in enantio-pure form, enabling the concise total synthesis of cylindricine C.

• Access to Document (DOI)

Asymmetric Total Synthesis of Fasicularin by Chiral N-Alkoxyamide Strategy

Yamamoto S., Komiya Y., Kobayashi A., Minamikawa R., Oishi T., Sato T., Chida N.

Organic Letters (Organic Letters)  21 ( 6 ) 1868 - 1871 2019.03

ISSN  15237060

　View Summary

© 2019 American Chemical Society. The asymmetric total synthesis of fasicularin is reported. The key to success is the use of a chiral N-alkoxyamide to control both reactivity and stereoselectivity. This functional group enables the aza-spirocyclization and the reductive Strecker reaction, which cannot be realized with an ordinary amide. In addition, use of the chiral alkoxy group establishes two consecutive stereocenters in the aza-spirocyclization through remote stereocontrol.

• Access to Document (DOI)

Unified Total Synthesis of Madangamine Alkaloids

Suto T., Yanagita Y., Nagashima Y., Takikawa S., Kurosu Y., Matsuo N., Miura K., Simizu S., Sato T., Chida N.

Bulletin of the Chemical Society of Japan (Bulletin of the Chemical Society of Japan)  92 ( 3 ) 545 - 571 2019

ISSN  00092673

　View Summary

© 2019 The Chemical Society of Japan. All rights reserved. The full details of a unified total synthesis of madangamine alkaloids are disclosed. Our central strategy is based on the construction of a common ABCE-tetracyclic system, followed by the late-stage installation of various D-rings. The common intermediate is assembled through N-acyliminium cyclization of a propargylsilane, and formation of the (Z,Z)-skipped diene. Stereoselective synthesis of the (Z,Z)-skipped diene is especially challenging, and is accomplished by the combination of Z-selective hydroboration of the 1,1-disubstituted allene and subsequent Migita-Kosugi-Stille coupling. Macrocyclic alkylation enables the late-stage variation of the D-rings on the common tetracyclic intermediate, resulting in the collective total syntheses of madangamines AE. The synthetic madangamine alkaloids exhibited inhibitory activities against a variety of human cancer cell lines.

• Access to Document (DOI)

Total synthesis of (–)-zephyranthine

Ishii K., Seki-Yoritate Y., Ishibashi M., Liaw M., Oishi T., Sato T., Chida N.

Heterocycles (Heterocycles)  99 ( 1 ) 111 - 117 2019

ISSN  03855414

　View Summary

© 2019 The Japan Institute of Heterocyclic Chemistry – Stereoselective total synthesis of (–)-zephyranthine 1 based on the chiral pool approach starting from D-arabinose is described. The three consecutive chiral centers in (–)-zephyranthine were effectively constructed by the sequential [3,3] sigmatropic rearrangements (Claisen, Overman, and Claisen rearrangements) with chirality transfer of the hydroxy groups in D-arabinose.

• Access to Document (DOI)

Iridium-catalyzed reductive nucleophilic addition to tertiary amides

Takahashi Y., Sato T., Chida N.

Chemistry Letters (Chemistry Letters)  48 ( 9 ) 1138 - 1141 2019

ISSN  03667022

　View Summary

© 2019 The Chemical Society of Japan. This article describes the development of an iridium-catalyzed reductive nucleophilic addition to tertiary amides. A conspicuous feature of this reaction is its high amide-selectivity via two processes: i) chemoselective hydrosilylation of amide carbonyls with Vaska’s complex [IrCl(CO)(PPh3)2] and (Me2HSi)2O, and ii) subsequent addition of a variety of mild nucleophiles to the resulting electrophilic iminium ions by the assistance of an acid. The reaction takes place in the presence of a variety of functional groups such as ester and nitro groups.

• Access to Document (DOI)

Enantioselective stereodivergent approach to α-hydroxy skipped dienes: Synthesis of the western polyene fragment of corallopyronin A

Nagashima Y., Okada Y., Sato T., Chida N.

Chemistry Letters (Chemistry Letters)  48 ( 12 ) 1519 - 1521 2019

ISSN  03667022

　View Summary

© 2019 The Chemical Society of Japan. Synthesis of the western polyene fragment of corallopyronin A is documented. The α-hydroxy skipped diene structure is stereoselectively synthesized by our method consisting of enantioselective allenylation of an aldehyde, hydroboration of the resulting 1, 1-disubstituted allene and Migita-Kosugi-Stille coupling. The developed approach could become a general platform for α-hydroxy skipped dienes embedded in a number of biologically active natural products because all eight stereoisomers of the α-hydroxy skipped diene are potentially available from the same aldehyde through these three stereodivergent reactions.

• Access to Document (DOI)

Iridium-Catalyzed Reductive Nucleophilic Addition to Secondary Amides

Takahashi Y., Yoshii R., Sato T., Chida N.

Organic Letters (Organic Letters)  20 ( 18 ) 5705 - 5708 2018.09

ISSN  15237060

　View Summary

Copyright © 2018 American Chemical Society. An iridium-catalyzed reductive nucleophilic addition to secondary amides is reported. After the iridium-catalyzed reduction, the resulting imines can undergo the Strecker reaction, the Mannich reaction, allylation, and [3 + 2]-cycloaddition. The method shows high chemoselectivity in the presence of other functional groups such as methyl ester.

• Access to Document (DOI)

Synthesis of β-Hydroxy-α,α-disubstituted Amino Acids through the Orthoamide-Type Overman Rearrangement of an α,β-Unsaturated Ester and Stereodivergent Intramolecular SN2′ Reaction: Development and Application to the Total Synthesis of Sphingofungin F

Sugai Tomoya, Usui Shunme, Tsuzaki Shun, Oishi Hiroki, Yasushima Daichi, Hisada Shoko, Fukuyasu Takahiro, Oishi Takeshi, Sato, Takaaki, CHIDA NORITAKA

Bulletin of the Chemical Society of Japan (Bulletin of the Chemical Society of Japan)  91 ( 4 ) 594 - 607 2018.04

Research paper (scientific journal), Accepted,  ISSN  00092673

　View Summary

© 2018 The Chemical Society of Japan. The development of a two-step synthesis for β-hydroxy-α,α- disubstituted amino acid derivatives from cyclic orthoamide is reported. The first step is the orthoamide-type Overman rearrangement of an α,β-unsaturated ester to give a sterically hindered α,α-disubstituted amidoester. The α,β-unsaturated ester is known to be a challenging substrate in the conventional Overman rearrangement due to the competitive aza-Michael reaction. However, suppression of the aza-Michael reaction is realized by two factors; 1) the high reaction temperature, and 2) an alkyl substituent at the α-position. The second step is stereodivergent intramolecular SN2′ reaction for the installation of a hydroxy group at the β-position. Either syn- or anti-type SN2′ reaction is possible by simply changing the reaction conditions. The developed method can provide all four possible stereoisomers of the β-hydroxy-α,α-disubstituted amino acid, and is successfully applied to the total synthesis of sphingofungin F.

• Access to Document (DOI)

Synthesis of Kaitocephalin Facilitated by Three Stereoselective Allylic Transposition Reactions

Sugai Tomoya, Okuyama Yuya, Shin Jaehyun, Usui Shunme, Hisada Shoko, Osanai Ryosuke, Oishi Takeshi, Sato Takaaki, CHIDA NORITAKA

Chemistry Letters (Chemistry Letters)  47 ( 4 ) 454 - 457 2018.04

Research paper (scientific journal), Joint Work, Accepted,  ISSN  03667022

　View Summary

© 2018 The Chemical Society of Japan. A stereoselective synthesis of kaitocephalin is described. The central strategy is based on chirality transfer reactions of three secondary alcohols derived from L-arabinose. The Overman rearrangement of an α,β-unsaturated ester, and intramolecular anti-type SN2¤ reaction constructed a β-hydroxy-α,α-disubstituted amino acid moiety. The third chirality transfer reaction is the Ichikawa rearrangement. These stereoselective reactions successfully established the three contiguous stereocenters embedded in kaitocephalin.

• Access to Document (DOI)

Stereodivergent Hydroboration of Allenes

Nagashima Yoshiyuki, Sasaki Keiji, Suto Takahiro, Sato Takaaki, CHIDA NORITAKA

Chemistry-An Asian Journal (Chemistry - An Asian Journal)  13 ( 8 ) 1024 - 1028 2018.04

Research paper (scientific journal), Joint Work, Accepted,  ISSN  18614728

　View Summary

© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Full details of a stereodivergent hydroboration of allenes are reported. While hydroboration of an allene with 9-BBN provided a thermodynamically stable (E)-allylic alcohol after oxidative work-up, the reaction of an identical allene with HB(Sia)2 (disiamylborane) formed a (Z)-allylic alcohol as the kinetic product. The developed conditions allowed for the synthesis of trisubstituted olefins in a highly stereoselective fashion, which is known to be challenging. The method was also applied to the stereodivergent synthesis of structural motifs such as skipped dienes and allylbenzenes, which are often embedded in biologically active natural products.

• Access to Document (DOI)

Crystal structure of (–)-(5R,7R,8S,9R,10S)-8- methyl-7-[(5R)-3-methyl-2-oxooxolan-3-en-5-yl]- 1-aza-6-oxatricyclo[8.3.0.05,9]tridecan-13-one monohydrate

Oishi Takeshi, Yoritate Makoto, Sato Takaaki, CHIDA NORITAKA

Acta Crystallographica, Section E (Acta Crystallographica Section E: Crystallographic Communications)  E74   555 - 558 2018.04

Research paper (scientific journal), Joint Work, Accepted

　View Summary

© 2018 Oishi et al. The title compound, C17 H23 NO4 ·H2 O, is an epimer of the natural tetracyclic alkaloid isosaxorumamide which consists of a fused 5-7-5 tricyclic core and a dihydrofuranone substituent. The terminal dihydrofuran ring is essentially planar with a maximum deviation of 0.0273(14)Å from the mean plane and oxolane, azepane and pyrrolidine rings in the tricyclic ring system adopt twist, twist-chair and envelope forms, respectively. In the crystal, the amide and water molecules are linked by O - H...O hydrogen bonds, forming a tape structure running along the b-axis direction. The tapes are further connected by C - H...O interactions into a three-dimensional architecture.

• Access to Document (DOI)

Crystal structure of (-)-(r,e)-3-(1,3-benzodioxol-5-yl)-5-[(4s,5r)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]-n,n-dimethylpent-4-enamide

Oishi T., Ishii K., Ishibashi M., Sato T., Chida N.

Acta Crystallographica Section E: Crystallographic Communications (Acta Crystallographica Section E: Crystallographic Communications)  74   825 - 828 2018

　View Summary

© 2018 International Union of Crystallography. All rights reserved. In the title compound, C 20 H 27 NO 6 , the amide moiety is essentially planar, with a maximum deviation of 0.073(3)Å, and one of the N-methyl groups shows rotational disorder. The five-membered 1,3-dioxolane ring adopts an envelope form, with the C atom bonded to the olefin side chain as the flap, which deviates from the mean plane through the other four atoms by 0.564(7)Å. The 1,3-dioxole ring fused to the benzene ring adopts a flattened envelope form, with the C atom between the two O atoms as the flap, which deviates from the mean plane through the other four atoms by 0.215(7)Å. The C-C=C-C olefin moiety is essentially planar and makes a dihedral angle of 87.1(3)° with the benzene ring. An intramolecular O-H O hydrogen bond supports the molecular conformation, enclosing an S(11) graph-set motif. In the crystal, intermolecular C-H O hydrogen bonding links the molecules into a tape running along the b axis. Furthermore, other weak C-H;O hydrogen bonds and a C-Hπ interaction connect the tapes into a sheet structure parallel to (100).

• Access to Document (DOI)

Total synthesis of complex alkaloids by nucleophilic addition to amides

Sato T., Yoritate M., Tajima H., Chida N.

Organic and Biomolecular Chemistry (Organic and Biomolecular Chemistry)  16 ( 21 ) 3864 - 3875 2018

ISSN  14770520

　View Summary

© 2018 The Royal Society of Chemistry. Nucleophilic addition to amides has been recognized as a promising transformation for total synthesis of complex alkaloids. Amides can accept two different organometallic reagents through the nucleophilic addition, which enables it to serve as a stable surrogate of multi-substituted amines. However, the nucleophilic addition has been overlooked for a long time due to three main reasons: low electrophilicity of amide carbonyls, potential hydrolysis of the reaction intermediate and excess addition of an organometallic reagent. This mini review focuses on the recent progress of total synthesis of complex alkaloids based on the nucleophilic additions to N-alkoxyamides, tertiary amides and secondary amides.

• Access to Document (DOI)

Unified Total Synthesis of Stemoamide-Type Alkaloids by Chemoselective Assembly of Five-Membered Building Blocks

Yoritate Makoto, Takahashi Yoshito, Tajima Hayato, Ogihara Chisato, Yokoyama Takashi, Soda Yasushi, Oishi Takeshi, Sato Takaaki, CHIDA NORITAKA

Journal of the American Chemical Society 139   18386 - 18391 2017.12

Research paper (scientific journal), Accepted

• Access to Document (DOI)

Reductive Approach to Nitrones from N-Siloxyamides and N-Hydroxyamides

Katahara Seiya, Kobayashi Shoichiro, Fujita Kanami, Matsumoto Tsutomu, Sato, Takaaki, CHIDA NORITAKA

Bulletin of the Chemical Society of Japan 90 ( 8 ) 893 - 904 2017.08

Research paper (scientific journal), Joint Work, Accepted

• Access to Document (DOI)

Crystal structure of (–)-methyl (R,E)-4-[(2R,4R)-2- amino-2-trichloromethyl-1,3-dioxolan-4-yl]-4-hydroxy-2-methylbut-2-enoate

Oishi Takeshi, Kidene Mayu,Sugai Tomoya, Sato Takaaki, CHIDA NORITAKA

Acta Crystallographica, Section E E73   983 - 986 2017.06

Research paper (scientific journal), Joint Work, Accepted

• Access to Document (DOI)

Unified Total Synthesis of Madangamines A, C, and E

T. Suto, Y. Yanagita, Y. Nagashima, S. Takikawa, Y. Kurosu, N. Matsuo, T. Sato, N. Chida

Journal of the American Chemical Society 139 ( 8 ) 2952 - 2955 2017.03

Research paper (scientific journal), Joint Work

Copper-catalyzed Electrophilic Amination Using N-Methoxyamines

Y. Fukami, T. Wada, T. Meguro, N. Chida, T. Sato

Organic & Biomolecular Chemistry 14 ( 24 ) 5486 - 5489 2016.06

Research paper (scientific journal), Joint Work, Accepted

Total Synthesis of (–)-Stemoamide by Sequential Overman/Claisen Rearrangement

Y. Nakayama, Y. Maeda, N. Hama, T. Sato, N. Chida

Synthesis 48 ( 11 ) 1647 - 1654 2016.06

Research paper (scientific journal), Joint Work, Accepted

N−アルコキシアミド基への求核付加反応の開発とゲフィロトキシンの全合成

佐藤 隆章，千田 憲孝

有機合成化学協会誌 74 ( 6 ) 599 - 610 2016.06

Research paper (scientific journal), Joint Work, Accepted

An Iridium-Catalyzed Reductive Approach to Nitrones from N-Hydroxyamides

S. Katahara, S. Kobayashi, K. Fujita, T. Matsumoto, T. Sato, #HN. Chida/U>

Journal of the American Chemical Society 138 ( 18 ) 5246 - 5249 2016.05

Research paper (scientific journal), Joint Work, Accepted

Crystal Structure of (+)-N-[(1R,5S,6S,9S)-5-Hydroxymethyl-3,3,9-trimethyl-8-oxo-2,4,7- trioxabicyclo[4.3.0]nonan-9-yl]acetamide

T. Oishi, S. Tsuzaki, T. Sugai, T. Sato, N. Chida

Acta Crystallographica, Section E E72   756 - 759 2016.05

Research paper (scientific journal), Joint Work, Accepted

Practical Synthesis of the C-Ring Precursor of Paclitaxel from 3-Methoxytoluene

K. Fukaya, Y. Yamaguchi, A. Watanabe, H. Yamamoto, T. Sugai, T. Sugai, T. Sato, N. Chida

The Journal of Antibiotics 69 ( 4 ) 273 - 279 2016.04

Research paper (scientific journal), Joint Work, Accepted

Crystal Structure of (+)-Methyl (E)-3-[(2S,4S,5R)-2-amino-5-hydroxymethyl-2-trichloromethyl-1,3-dioxolan-4-yl]-2-methylprop-2-enoate

Takeshi Oishi, Daichi Yasushima, Kihiro Yuasa, Takaaki Sato, and Noritaka Chida

Acta Crystallographica, Section E E72   343 - 346 2016.03

Research paper (scientific journal), Joint Work, Accepted

• Access to Document (DOI)

Enantioselective Total Synthesis of (+)-Neostenine

Yasuaki Nakayama, Yuichiro Maeda, Masayuki Kotatsu, Ruriko Sekiya, Masato Ichiki, Takaaki Sato, and Noritaka Chida

Chemistry-A European Journal 22 ( 10 ) 3300 - 3303 2016.03

Research paper (scientific journal), Joint Work, Accepted

• Access to Document (DOI)

Synthesis of (+/–)-Lasubine II Utilizing N-Methoxyamines

Takashi Yokoyama, Yutaro Fukami, Takaaki Sato, and Noritaka Chida

Chemistry-An Asian Journal 11 ( 4 ) 470 - 473 2016.02

Research paper (scientific journal), Joint Work, Accepted

Crystal Structure of (+/–)-(5SR,6SR)-6-Ethenyl-1-[(RS)-1-phenylethoxy]-1- azaspiro[4.5]decan-2-one

Takeshi Oishi, Shio Yamamoto, Takashi Yokoyama, Akihiro Kobayashi, Takaaki Sato, and Noritaka Chida

Acta Crystallographica, Section E E71   1528 - 1530 2015.12

Research paper (scientific journal), Joint Work, Accepted

• Access to Document (DOI)

Crystal Structure of (+/–)-(7SR,8SR)-7-Methyl-1,4-dioxa-spiro[4.5]decane-7,8-diol

Takeshi Oishi, Hiroaki Yamamoto, Tomoya Sugai, Keisuke Fukaya, Yu Yamaguchi, Ami Watanabe, Takaaki Sato, and Noritaka Chida

Acta Crystallographica, Section E E71   1181 - 1184 2015.10

Research paper (scientific journal), Joint Work, Accepted

• Access to Document (DOI)

Synthesis of Paclitaxel. 2. Construction of the ABCD Ring and Formal Synthesis

Keisuke Fukaya, Keisuke Kodama, Yuta Tanaka, Hirohisa Yamazaki, Tomoya Sugai, Yu Yamaguchi, Ami Watanabe, Takeshi Oishi, Takaaki Sato, and Noritaka Chida

Organic Letters 17 ( 11 ) 2574 - 2577 2015.06

Research paper (scientific journal), Joint Work, Accepted

• Access to Document (DOI)

Synthesis of Paclitaxel. 1. Synthesis of the ABC Ring of Paclitaxel by SmI2-Mediated Cyclization

Keisuke Fukaya, Yuta Tanaka, Ayako C. Sato, Keisuke Kodama, Hirohisa Yamazaki, Takeru Ishimoto, Yasuyoshi Nozaki, Yuki M. Iwaki, Yohei Yuki, Kentaro Umei, Tomoya Sugai, Yu Yamaguchi, Ami Watanabe, Takeshi Oishi, Takaaki Sato, and Noritaka Chida

Organic Letters 17 ( 11 ) 2570 - 2573 2015.06

Research paper (scientific journal), Joint Work, Accepted

• Access to Document (DOI)

Crystal Structure of (+/–)-(1SR,5SR,6SR,7SR,10SR,11SR,13SR)-13-Benzyloxy-7-methoxymethoy-11,15,18,18-tetramethyl- 3-oxo-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadeca-14-16-dien-10-yl Benzoate

Takeshi Oishi, Keisuke Fukaya, Yu Yamaguchi, Tomoya Sugai, Ami Watanabe, Takaaki Sato, and Noritaka Chida

Acta Crystallographica, Section E E71   490 - 493 2015.04

Research paper (scientific journal), Joint Work, Accepted

• Access to Document (DOI)

Synthesis of Diazatricyclic Common Structure of Madangamine Alkaloids

Yuta Yanagita, Takahiro Suto, Naoya Matsuo, Yasuhiro Kurosu, Takaaki Sato, and Noritaka Chida

Organic Letters 17 ( 8 ) 1946 - 1949 2015.04

Research paper (scientific journal), Joint Work, Accepted

• Access to Document (DOI)

Total Synthesis of (+/–)-Gephyrotoxin and (+/–)-Perhydrogephyrotoxin

Kenji Shirokane, Yuya Tanaka, Makoto Yoritate, Nobuaki Takayama, Takaaki Sato, andNoritaka Chida

Bulletin of the Chemical Society of Japan 88 ( 4 ) 522 - 537 2015.04

Research paper (scientific journal), Joint Work, Accepted

• Access to Document (DOI)

Crystal Structure of (+/–)-(1SR,5SR,6SR,7SR,10SR,11SR,13RS,14SR)-13-Hydroxy-7-methoxymethoxy- 11,15,18,18-tetramethyl-3-oxo-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadec-15-en-10-yl Benzoate, Its 13-Epimer and 13-One Derivative

Takeshi Oishi, Keisuke Fukaya, Yu Yamaguchi, Tomoya Sugai, Ami Watanabe, Takaaki Sato, and #HNoritaka Chida#H

Acta Crystallographica, Section E E71   466 - 472 2015.04

Research paper (scientific journal), Joint Work, Accepted

• Access to Document (DOI)

Total Synthesis of Sphingofungin F by Orthoamide-Type Overman Rearrangement of an Unsaturated Ester

Shun Tsuzaki, Shunme Usui, Hiroki Oishi, Daichi Yasushima, Takahiro Fukayasu, Takeshi Oishi, Takaaki Sato, Noritaka Chida

Organic Letters 17 ( 7 ) 1704 - 1707 2015.04

Research paper (scientific journal), Joint Work, Accepted

• Access to Document (DOI)

Indium-Catalyzed Chemoselective Reductive Nucleophilic Addition to N-Methoxyamides

Minami Nakajima, Takaaki Sato, Noritaka Chida

Organic Letters 17 ( 7 ) 1696 - 1699 2015.04

Research paper (scientific journal), Joint Work

• Access to Document (DOI)

Crystal Structure of (+/-)-(4RS,5RS,7SR)-4-[(1RS,2RS,3RS,6RS)-3-benzoyloxy-2-(2-hydroxyethyl)-6-methoxymethoxy-2-methylcyclohexyl]-8,10,10,trim ethyl-2-oxo-1,3-dioxaspiro[4.5]dec-8-en-7-yl Benzoate Benzene Monosolvate

Takishi Oishi, Yuu Yamaguchi, Keisuke Fukaya, Tomoya Sugai, Ami Watanabe, Takaaki Sato, Noritaka Chida

Acta Crystallographica Section E E71   8 - 11 2015.01

Research paper (scientific journal), Accepted

• Access to Document (DOI)

Chemoselective Reductive Nucleophilic Addition to Tertiary Amides, Secondary Amides, and N-Methoxyamides

Minami Nakajima, Yukiko Oda, Takamasa Wada, Ryo Minamikawa, Kenji Shirokane, Takaaki Sato, Noritaka Chida

Chemistry A European Journal 20 ( 52 ) 17565 - 17571 2014.12

Research paper (scientific journal), Joint Work, Accepted

• Access to Document (DOI)

Synthesis of Natural Products Containing Cyclohexane Units Utilizing the Ferrier Carbocyclization Reaction

Noritaka Chida, Takaaki Sato

The Chemical Record 14 ( 4 ) 592 - 605 2014.08

Research paper (scientific journal), Joint Work, Accepted

• Access to Document (DOI)

(5R*)-5-[(2S*,5S*)-1-Methoxy-5-phenylpyrrolidin-2-yl]-3-methylfuran-2(5H)-one

Takeshi Oishi, Makoto Yoritate, Takaaki Sato, Noritaka Chida

Acta Crystallographica Section E E70   o839 2014.07

Research paper (scientific journal), Accepted

• Access to Document (DOI)

Two-step Synthesis of Multi-Substituted Amines by Using an N-Methoxy Group as a Reactivity Control Element

Makoto Yoritate, Tatsuhiko Meguro, Naoya Matsuo, Kenji Shirokane, Takaaki Sato, Noritaka Chida

Chemistry A European Journal 20 ( 26 ) 8210 - 8216 2014.06

Research paper (scientific journal), Joint Work, Accepted

• Access to Document (DOI)

Nucleophilic Addition to N-Alkoxyamides

CHIDA NORITAKA

Organic and Biomolecular Chemistry (The Royal Society of Chemistry)  12 ( 20 ) 3147 - 3150 2014.05

Research paper (scientific journal), Joint Work, Accepted

Total Synthesis of (+/-)-Gephyrotoxin by Amide-Selective Reductive Nucleophilic Addition

CHIDA NORITAKA

Angewandte Chemie International Edition (Wiley-VCH)  53 ( 2 ) 512 - 516 2014.01

Research paper (scientific journal), Joint Work, Accepted

Cascade- and Orthoamide-Type Overman Rearrangements of Allylic Vicinal Diols

CHIDA NORITAKA

Chemistry A European Journal (Wiley-VCH)  19   12052 - 12058 2013.09

Research paper (scientific journal), Joint Work, Accepted

Direct Nucleophilic Addition to N-Alkoxyamides

Yanagita, Y.; Nakamura, H.; Shirokane, K.; Kurosaki, Y.; Sato, T.; Chida, N.

Chemistry A European Journal 19 ( 2 ) 678-684 2013.01

Research paper (scientific journal), Joint Work, Accepted

Synthesis of (–)-Morphine: Application of Sequential Claisen/Claisen Rearrangement of an Allylic Vicinal Diol

Ichiki, M.; Tanimoto, H.; Miwa, S.; Saito, R.; Sato, T.; Chida, N.

Chemistry A European Journal 19 ( 1 ) 264-269 2013.01

Research paper (scientific journal), Joint Work, Accepted

(+)-(1S,5R,6R)-6-[(S)-1-Hydroxy-2-(methoxymethyloxy)ethyl]-1-methyl-3-trichloromethyl-2-aza-4,7-dioxabicyclo-[3.3.0]oct-2-en-8-one

Oishi, T.; Oishi, H.; Tsuzaki, S.; Sato, T.; Chida, N.

Acta Crystallographica Section E 68   3185 2012.08

Research paper (scientific journal), Joint Work, Accepted

Chirality Transfers through Sequential Sigmatropic Rearrangements of Allylic Vicinal Diols: Development and Application to Total Synthesis of (–)-Kainic Acid

Kitamoto, K.; Nakayama, Y.; Sampei, M.; Ichiki, M.; Furuya, N.; Sato, T.; Chida, N.

European Journal of Organic Chemistry  ( 22 ) 4217-4231 2012.06

Research paper (scientific journal), Joint Work, Accepted

Concise Synthesis of α-Trisubstituted Amines from Ketones Using N-Methoxyamines

Kurosaki, Y.; Shirokane, K.; Oishi, T.; Sato, T.; Chida, N.

Organic Letters 14 ( 8 ) 2098-2101 2012.04

Research paper (scientific journal), Joint Work, Accepted

Direct Chemoselective Allylation of Inert Amide Carbonyls

CHIDA NORITAKA

Organic Letters 14 ( 3 ) 950-953 2012.02

Research paper (scientific journal), Joint Work

Total Synthesis of Broussonetine F: The Orthoamide Overman Rearrangement of an Allylic Diol

CHIDA NORITAKA

Organic Letters 13 ( 4 ) 616-619 2011.02

Research paper (scientific journal), Joint Work, Accepted

Total Synthesis of (-)-Salinosporamide A

CHIDA NORITAKA

Chemistry an Asian Journal 6 ( 1 ) 209-219 2011.01

Research paper (scientific journal), Joint Work, Accepted

Total Synthesis of (+)- and (-)-Galanthamine

CHIDA NORITAKA

Heterocycles 82 ( 1 ) 563-579 2010.12

Research paper (scientific journal), Joint Work, Accepted

Novel Sequential Sigmatropic Rearrangements of Allylic Diols: Application to the Total Synthesis of (-)-Kainic Acid

CHIDA NORITAKA

Organic Letters 12 ( 24 ) 5756-5759 2010.12

Research paper (scientific journal), Joint Work, Accepted

A Direct Entry to Substituted N-Methoxyamines from N-Methoxyamides via N-Oxyiminium Ions

CHIDA NORITAKA

Angewandte Chemie International Edition 49 ( 36 ) 6369-6372 2010.08

Research paper (scientific journal), Joint Work, Accepted

Total Synthesis of Mycestericin A and Its 14-Epimer

Yamanaka Hiroyoshi, Sato Kazuya, Sato Hideyuki, Iida Masatoshi, Oishi Takeshi, CHIDA NORITAKA

Tetrahedron 65 ( 45 ) 9188-9201 2009.11

Research paper (scientific journal), Joint Work, Accepted

Formal Synthesis of Salinosporamide A Starting from D-Glucose

Momose Takayuki, Kaiya Yuji, Hasegawa Jun-ichi, Sato Takaaki, CHIDA NORITAKA

Synthesis 2009 ( 17 ) 2983-2991 2009.09

Research paper (scientific journal), Joint Work, Accepted

Total Synthesis of (-)-Agelastatin A: The Application of a Sequential Sigmatropic Rearramgement

Hama Naoto, Matsuda Tomoki, Sato Takaaki, CHIDA NORITAKA

Organic Letters 11 ( 12 ) 2687-2690 2009.06

Research paper (scientific journal), Joint Work, Accepted

Total Synthesis of Nucleoside Antibiotics Possessing Novel N-Glycoside Structures

CHIDA NORITAKA

Journal of Synthetic Organic Chemistry, Japan 66 ( 11 ) 1105-1115 2008.11

Research paper (scientific journal), Single Work, Accepted

カチオン-π相互作用を利用した有機合成化学

CHIDA NORITAKA

化学 63 ( 8 ) 66-67 2008.08

Research paper (scientific journal), Joint Work

Total Synthesis of (+/-)-Murrayazoline

CHIDA NORITAKA

Organic Letters 10 ( 10 ) 1999-2002 2008.05

Research paper (scientific journal), Joint Work, Accepted

Total Synthesis of Mycestericin A

CHIDA NORITAKA

Tetrahedron Letters 49 ( 12 ) 1943-1947 2008.03

Research paper (scientific journal), Joint Work, Accepted

Total Synthesis of A-315675 Base on the Cascade Overman Rearrangement

CHIDA NORITAKA

Tetrahedron Letters 49 ( 8 ) 1376-1379 2008.02

Research paper (scientific journal), Joint Work, Accepted

Formal Synthesis of (-)-Morphine from D-Glucal Based on the Cascade Claisen Rearrangement

CHIDA NORITAKA

Tetrahedron Letters 49 ( 2 ) 358-362 2008.01

Research paper (scientific journal), Joint Work, Accepted

Total Synthesis of (+)-Galanthamine Starting from D-Glucose

CHIDA NORITAKA

Tetrahedron Letters 48 ( 36 ) 6267-6270 2007.09

Research paper (scientific journal), Joint Work, Accepted

Total Synthesis of Amaryllidaceae Alkaloids, (+)-Vittatine and (+)-Haemanthamine, Starting from D-Glucose

CHIDA NORITAKA

Tetrahedron 63 ( 30 ) 6977-6989 2007.07

Research paper (scientific journal), Joint Work, Accepted

Total Synthesis of Dapiramicin B

CHIDA NORITAKA

Tetrahedron Letters 47 ( 32 ) 5747-5750 2006.08

Research paper (scientific journal), Joint Work, Accepted

One-step Construction of Carbazoles by way of the Palladium-catalyzed Double N-Arylation Reaction and Its Application to the Total Synthesis of Murrastifoline-A

CHIDA NORITAKA

Tetrahedron 62 ( 29 ) 6792-6801 2006.07

Research paper (scientific journal), Joint Work

Total Synthesis of Actinobolin from D-Glucose by way of the Stereoselective Three-component Coupling Reaction

CHIDA NORITAKA

Tetrahedron 62 ( 29 ) 6926-6944 2006.07

Research paper (scientific journal), Joint Work

Total Synthesis of Stevastelins: Structure Confirmation of Stevastelins B and B3, and Structure Revision of Stevastelin C3

CHIDA NORITAKA

Bulletin of the Chemical Society of Japan 79 ( 6 ) 921-937 2006.06

Research paper (scientific journal), Joint Work, Accepted

Total Synthesis of Murrastifoline-A by Way of the Pd-Catalyzed Double N-Arylation of a Carbazolamine with a 2,2'-Dibrmobiphenyl Derivative

CHIDA NORITAKA

Heterocycles 65 ( 7 ) 1561-1567 2005.07

Research paper (scientific journal), Joint Work, Accepted

Total Synthesis of Stevastelins B3 and C3: Structure Confirmation of Stevastelin B3 and Revision of Stevastelin C3

CHIDA NORITAKA

Tetrahedron Letters 46 ( 3 ) 389-392 2005.01

Research paper (scientific journal), Joint Work

Total Synthesis and Biological Activities of (+)-Sulfamisterin (AB5366) and its Analogues

CHIDA NORITAKA

The Journal of Antibiotics 58 ( 1 ) in press 2005.01

Research paper (scientific journal), Joint Work

Overman転位反応を鍵反応とした糖質からのα-置換α-アミノ酸構造を有する天然物の全合成

CHIDA NORITAKA

Journal of Synthetic Organic Chemistry, Japan 62 ( 7 ) 693-704 2004.07

Research paper (scientific journal), Joint Work, Accepted

A New Entry to Amaryllidaceae Alkaloids from Carbohydrates: Total Synthesis of (+)-Vittatine

CHIDA NORITAKA

Chemical Communications  ( 9 ) 1086-1087 2004.04

Research paper (scientific journal), Joint Work, Accepted

New Synthesis of (-)- and (+)-Actinobolin from D-Glucose

CHIDA NORITAKA

Tetrahedron Letters 44 ( 27 ) 5047-5051 2003.06

Research paper (scientific journal), Joint Work, Accepted

The New and Efficient Synthesis of Heptose Moiety of Spicamycin

CHIDA NORITAKA

Chemistry Letters 32 ( 2 ) 190-191 2003.02

Research paper (scientific journal), Joint Work, Accepted

(+)-(1S,2S,4S,4aR,5R,6S,9S,10S)-4-Benzyloxy-9,10-(carbonyldioxy)-1-methoxymethoxy-4a,6,8,8-tetramethyl-7-methylenedodecahydro-6,9-ethanobenzocyclooctene-5-ol

CHIDA NORITAKA

Acta Crystallographica Section E E59 ( 12 ) o1476-o1477 2003

Research paper (scientific journal), Joint Work, Accepted

(+)-Methyl (4R,5S)-4-[(R)-1-hydroxybut-3-enyl]-5,2,2-dimethyl-trichloroacetamido-1,3-dioxane-5-carboxylate

CHIDA NORITAKA

Acta Crystallographica Section E E59 ( 12 ) o1259-o1260 2003

Research paper (scientific journal), Joint Work, Accepted

Total Synthesis of (+)-Myriocin and (-)-Sphingofungin E from Aldohexoses Using Overman Rearrangement as the Key Reaction

CHIDA NORITAKA

Bulletin of the Chemical Society of Japan 75 ( 9 ) 1927-1947 2002.09

Research paper (scientific journal), Joint Work, Accepted

Total Synthesis of (-)-Stevastelin B

CHIDA NORITAKA

Chemical Communications  ( 13 ) 1280-1281 2002.06

Research paper (scientific journal), Joint Work, Accepted

Total Synthesis of Spicamycin

CHIDA NORITAKA

The Journal of Organic Chemistry 67 ( 9 ) 2874-2880 2002.05

Research paper (scientific journal), Joint Work, Accepted

Total Synthesis of Sphingofungin E from D-Glucose

大石　毅，安藤幸司，伊野宮憲人，佐藤英之，飯田正俊

Organic Letters　 Vol. 4   151-154 2002.01

Joint Work

　View Summary

抗真菌活性を有し，α?置換アミノ酸構造を持つ天然物，スフィンゴフンギンＥの全合成に関する報告。

2-Chloro-4-(4-methoxybenzyloxy)pyrimidine

CHIDA NORITAKA

Acta Crystallographica Section E E58 ( 10 ) 1200-1201 2002

Research paper (scientific journal), Joint Work, Accepted

Stereoselective Total Synthesis of(+)-Myriocin from D-Mannose

大石　毅，安藤幸司

Chemical 　Communications    1392-1933 2001.09

Joint Work

　View Summary

強い免疫抑制活性を有する天然物，ミリオシンをD-マンノースを出発原料として全合成した。

Chiral Synthesis of the CD Ring Unit of Paclitaxel from D-Glucal

百瀬孝幸、瀬戸口正樹、藤田俊樹、田村仁

Chemical Communications    2237-2238 2000.11

Joint Work

　View Summary

強い抗腫瘍活性を有し、複雑な構造を持つパクリタキセル（タキソール）のＣＤ環部をD-グルカールを出発原料として、立体選択的に合成した。

myo-イノシトールの環開裂反応を利用した天然物合成

有機合成化学協会誌 Vol. 58   642-653 2000.07

Single Work

　View Summary

天然に豊富に存在するmyo-イノシトールのシクロヘキサン環を開裂させ、キラル素子を合成、これらを利用した天然物合成の最近の進歩について述べた総説。

(2S,3R,4S,5R,6S)-6-Benzyloxymethyl-4-(methoxymethyloxy)-9-oxo-8-oxa-1-azabicyclo[4.3.0]nonane-2,3,5-triyltriacetate

大場茂、大石毅、安藤幸司、伊野宮憲人

Acta Crystallographica Section C Vol. C56   223 2000.05

Joint Work

　View Summary

抗真菌活性を有する天然物、スフィンゴフンギンEの合成中間体のＸ線構造解析に関する報告。

(1R,2R,3S,4S)-2-[(2R,3S)-2,3-　Dimethyloxiran-2-yl]-3,4-bis(4-　Methoxybenzyloxy)cyclohexanol

大場茂、天野誠司、小川典子、大塚雅己

Acta Crystallographica Section C Vol. C56   222 2000.05

Joint Work

　View Summary

免疫抑制活性を有するFR65814物質の全合成における中間体のX線構造解析に関する報告。

Total Synthesis of Spicamycin Amino Nucleoside

鈴木保、田中さやか、山田巌、小足嘉昭、山田和恵

Organic Letters Vol. 2   1137-1140 2000.04

Joint Work

　View Summary

放線菌から単離され、強い抗腫瘍活性を有するスピカマイシンの母核化合物である表題化合物を初めて全合成し、その推定絶対構造が正しいことを示した。

Total Synthesis of Paniculide A from D-Glucose

Tetrahedron Vol. 55   3855-3870 1999.03

Joint Work

Pd-Catalyzed Coupling Reaction of Glycosylamines with 6-Chloropurines: Synthesis of 6-(b-D-Mannopyranosylamino)-9H-purine and its b-D-Gluco Isomer, N-Glycoside Models for Spicamycin and Septacidin

Tetrahedron Lett. Vol. 40   2573-2576 1999.03

Joint Work

Chiral and Stereoselective Total Synthesis of Novel Immunosuppressant FR65814 from D-Glucose

Tetrahedron Vol. 55   2205-2224 1999.02

Joint Work

植物由来のシクリトール類を出発原料とした天然物合成

千田憲孝

ファルマシア 34 ( 11 ) 1107-1111 1998.11

Research paper (scientific journal), Single Work

　View Summary

天然に豊富に存在するシクリトール類を利用した天然物合成に関する総説（日本語）．（5頁）

Total Synthesis and Absolute Configuration of FR65814

天野誠司、小川典子、大塚雅己、小川誠一郎、千田憲孝

Chem. Commun.  1998.06

Joint Work

　View Summary

免疫抑制活性を示す天然セスキテルペン、ＦＲ65814をD-グルコースを原料として、初めて全合成した．炭素環形成反応、クライゼン転位、パラジウムによるカップリング反応を利用した．本合成により、絶対構造を確定することに成功した．（2頁）

Total Synthesis of Acanthacerebroside A and Astrocerebroside A via a Chiral Epoxide Intermediate Derived from L-Quebrachitol

千田憲孝、阪田登、村井克之、戸部貴彦、長瀬俊彦、小川誠一郎．

Bull. Chem. Soc. Jpn. 71  1998.01

Joint Work

　View Summary

複合糖脂質であり、抗腫瘍活性を示す海産セレブロシド、アカンタセレブロシドＡ、アストロセレブロシドＡをＬ-クェブラキトールから誘導される光学活性エポキシドを共通の中間体として、全合成した．この合成により、絶対構造を確認できた．また糖脂質の新しい合成法を開発することができた．（14頁）

Stereoselective Total Synthesis of (+)-Lactacystin from D-Glucose

千田憲孝、武岡準、堤紀子、安藤幸司、小川誠一郎

Tetrahedron 53  1997.12

Joint Work

　View Summary

神経栄養因子活性を示し、興味あるα、α－二置換αアミノ酸構造を持つラクタシスチンをＤ-グルコースから全合成した．Overman 転位反応により窒素を含む４置換炭素を立体選択的に構築した．（12頁）

Synthetic Study on Natural Products Containing a,a-Disubstituted a-Amino Acid Structures Starting from Carbohydrates-Total Synthesis of Lactacystin-

千田憲孝，武岡準，安藤幸司，堤紀子，小川誠一郎

The Seventh International Kyoto Conference on New Aspects of Organic Chemistry  1997.11

Joint Work, Accepted

　View Summary

α，α-２置換αアミノ酸構造を有する天然物を入手容易な炭水化物から立体選択的に合成する方法論の開発と，本方法論を利用した，ラクタシスチンの全合成に関する報告

Total Synthesis of (-)-PA48153C (Pironetin) Utilising L-Quebrachitol as a Chiral Building Blick

千田憲孝、吉永光周、戸部貴彦、小川誠一郎

Chem. Commun.  1997.06

Joint Work

　View Summary

免疫抑制活性を示す天然物、PA48153C をＬ－クェブラキトールを出発原料として、高立体選択的に全合成した．クェブラキトールへのメチル基の導入と位置選択的な環開裂反応、ジチアン－エポキシカップリングを鍵反応として用いた．（2頁）

Synthesis of Acyclic and Heterocyclic Natural Products Utilizing Cyclitols as Novel Chiral Building Block

千田憲孝、小川誠一郎

Chem. Commun.  ( 9 ) 807-813 1997.05

Research paper (scientific journal), Joint Work

　View Summary

天然に豊富に存在するシクリトール類を出発原料として用い、これを立体選択的に官能基化したのちに、シクロヘキサン環を位置選択的に開裂させる手法の開発と天然物合成への応用についての総説．（7頁）

Synthetic Study on Sesquiterpenoids Possessing Cyclohexane Unit Starting from Aldohexoses

天野誠司，武村憲昭，小川典子，小川誠一郎，千田憲孝

Seventh Asian Chemical Congress  1997.05

Joint Work, Accepted

　View Summary

天然に豊富に存在するアルドヘキソース類を出発原料として用い，シクロヘキサン骨格を有する天然セスキテルペン（パニクリドA，FR65814）を全合成した。

Chiral and Stereoselective Total Synthesis of (-)-Mesembranol starting from D-Glucose

千田憲孝、杉原宏治、天野誠司、小川誠一郎

J. Chem. Soc., Perkin Trnas, 1  1997.01

Joint Work

　View Summary

４級炭素を含む興味ある構造を有するアルカロイド、メセンブラノールをＤ－グルコースから立体選択的に全合成した．４級炭素構築にはクライゼン転位を、骨格合成には分子内アミノマーキュレーションを活用した．（６頁）

Total Synthesis of (+)-7-Deoxy-pancratistatin and (+)-7-Deoxy-trans-dihydronarciclasine

千田憲孝、実岡誠、山本義之、大塚雅己、小川誠一郎

Heterocycles 43  1996.07

Joint Work

　View Summary

極めて強い細胞毒性をしめす天然アルカロイド、７－デオキシパンクラチスタチンをＤ－グルコースから立体選択的に全合成した．合成中間体からトランスジヒドロナルシクラシンも合成することに成功した．（6頁）

Synthesis of the Precursor of Rectricticin and Restrictinol Utilizing L-Quebrachitol as a Chiral Building Block

千田憲孝、戸部貴彦、吉永光周、大坂耕一郎、小川誠一郎

Carbohydr. Lett. 2  1996.06

Joint Work

　View Summary

L-クェブラキトールに立体選択的にアルキル基を導入後、シクロヘキサン環を位置選択的に開裂させる手法により、抗真菌性抗生物質レストリクチシンの合成中間体を合成した．（6頁）

Tremorgenic Indole Alkaloids. 9. Asymmetric Construction of an Advanced F-G-H-Ring Lactone Precursor for the Synthesis of Penitrem D

A. B. Smith, III, E. G. Nolen, Jr., R. Shirai, F. R.Blawe, M. Ohta, N. Chida, R. A. Hartz, D. M. Fitch,W. M. Clark, and　P. A. Sprengeler.

J. Org. Chem. 60  1995.12

Joint Work

　View Summary

新規アルカロイドであるペニトレム類の全合成に有用であると考えられる中間体、３環性ラクトンの効率的な合成に関する報告．（12頁）

Utilization of myo-Inositol in Higher Carbon Sugar Synthesis: Total Synthesis of Methyl Penta-N,O-acetyl-a-D-lincosaminide

千田憲孝、中澤圭一、二宮里江、天野誠司、小泉和枝、稲葉純子、小川誠一郎．　

Carbohydr. Lett. 1  1995.11

Joint Work

　View Summary

myo-イノシトールを原料とした多炭糖の合成の試み．抗生物質リンコマイシンの構成８炭糖である表題化合物の立体選択的な全合成に成功した．（8頁）

アルドへキソース類を出発原料としたシクロヘキサン骨格を有する天然物の合成

千田憲孝、小川誠一郎

有機合成化学協会誌 53 ( 10 ) 858-868 1995.10

Research paper (scientific journal), Joint Work, Accepted

　View Summary

糖質を対応するシクロヘキサノールへ変換するFerrier 環化反応の効率化と本反応を利用したシクロヘキサン骨格を有する天然物の合成に関する総説（日本語）．（10頁）

Synthesis of (+)-Fortamine from L-Quebrachitol

小川誠一郎、大館明男、大西賢牛、谷川哲也、木村洋、千田憲孝．

Carbohydr. Lett. 1  1995.06

Joint Work

　View Summary

抗生物質フォルティミシンＡの構成アミノシクリトールである表題化合物をＬ－クェブラキトールから合成した．（6頁）

Total Synthesis and Absolute Configuration of Sphingofungin D (N-Acetyl Asperfungin)

千田憲孝、池本裕之、野口愛乃、天野誠司、小川誠一郎

Natural Prod. Lett. 6  1995.05

Joint Work

　View Summary

抗真菌活性を有するスフィンゴフンギンＤをエポキシオクタン、myo-イノシトールを出発原料として全合成した．本合成により、未決定であった１４位の立体化学も含め、絶対銅像が確定された．（8頁）

Total Synthesis of (+)-Lactacystin from D-Glucose

千田憲孝、武岡準、堤紀子、小川誠一郎

J. Chem. Soc.,Chem. Commun.  1995.04

Joint Work

　View Summary

神経栄養因子活性を有する新規アミノ酸誘導体、ラクタシスチンをＤ－グルコースを出発原料とし、立体選択的なOverman 転位反応を鍵反応として全合成した．（2頁）

Synthesis of Carbocyclic Analogues of 3-DeoxyD-manno-2-octulosonic Acid and N-Acetylneuraminic Acid

小川誠一郎、吉川将、瀧敏明、横井重喜、千田憲孝

Carbohydr. Res. 269  1995.04

Joint Work

　View Summary

Ｎ－アセチルノイラミン酸、ならびに３-デオキシ－マンノ-２-オクツロン酸の環内酸素原子を炭素原子に置き換えた類縁体の全合成の報告．（26頁）

「計算化学」に関する参考書

千田憲孝

ファルマシア　31  1995

Single Work

　View Summary

ブックガイド．計算化学に関する最近の著書についての紹介．（1頁）

Stereoselective Conversion of L- Quebrachitol into a Novel Hydroxylated Caprolactam: Total Synthesis of Bengamide B

千田憲孝、戸部貴彦、村井克之、山崎香、小川誠一郎

Heterocycles 38  1994.11

Joint Work

　View Summary

抗寄生虫活性を示す新規海産天然物、ベンガミドＢの７員環ラクタム部をＬ－クェブラキトールへ立体選択的に窒素原子を導入する手法により合成し、ベンガミドＢの全合成を達成した．（6頁）

Regioselective Baeyer-Villiger Reaction of Polyhydroxycyclohexanone Derivatives

千田憲孝、戸部貴彦、小川誠一郎

Tetrahedron Lett. 35  1994.09

Joint Work

　View Summary

ポリヒドロキシ構造を有するシクロヘキサノン誘導体のBaeyer-Villiger 反応が高位置選択的に進行することを見いだした．置換基の種類と炭素原子の転位の傾向についての議論も行った．（4頁）

Synthesis of (+)-Galactostatin and (+)-1-Deoxygalactostatin utilizing L-Quebrachitol as a Chiral Building Block

千田憲孝、谷川哲也、戸部貴彦、小川誠一郎

J. Chem. Soc.,Chem. Commun.  1994.05

Joint Work

　View Summary

天然に豊富に存在する光学活性シクリトールであるＬ－クェブラキトールを利用し、位置選択的な環開裂反応を用いて、酵素阻害活性を有する表題化合物を立体選択的に全合成した．（2頁）

Chiral Synthesis of (-)-Mesembranol Starting from D-Glucose

千田憲孝、杉原宏治、小川誠一郎

J. Chem. Soc.,Chem. Commun.  1994.04

Joint Work

　View Summary

４級炭素を有し、特徴ある構造を有する天然アルカロイドメセンブラノールをD-グルコースの環化反応、クライゼン転位による効率的な４級炭素構築などを鍵反応として全合成した．（2頁）

Total Synthesis of (+)-Polyoxin J Starting from myo-Inositol

千田憲孝、小泉和枝、北田陽子、横山千秋、小川誠一郎

J. Chem. Soc., Chem. Commun.  1994.01

Joint Work

　View Summary

抗真菌性抗生物質であるポリオキシンＪを天然に豊富に存在するmyo-イノシトールを出発原料として全合成した．位置選択的な環開裂反応が有効な合成手法であることを明らかにした．（3頁）

Utilsation of L-Quebrachitol in Natural Product Synthesis. Total Synthesis and Absolute Configuration of (-)-Oudemansin X

千田憲孝、山田研、小川誠一郎

J. Chem. Soc., Perkin Trans. 1  1993.08

Joint Work

　View Summary

天然に豊富に存在する光学活性シクリトールであるＬ－クェブラキトールを利用した天然物合成の例．抗真菌活性を有するオウデマンシンＸの初めての全合成を達成し、その絶対構造を確定した．（6頁）

Total Synthesis of (+)-Lycoricidine and Its 2-Epimer from D-Glucose

千田憲孝、大塚雅巳、小川誠一郎

J. Org. Chem. 58  1993.07

Joint Work

　View Summary

抗腫瘍活性を示す天然アルカロイド、リコリシジンをD-グルコースを出発原料として全合成した．新規に開発された糖質の炭素環形成反応、パラジウムを用いる分子内環化反応を鍵反応として用いた．（7頁）

Synthesis of (+)- and (-)-Nojirimycin amd Their 1-Deoxy Derivatives from myo-Inositol

千田憲孝、古野由佳、池本裕之、小川誠一郎

Carbohydr. Res. 237  1992.12

Joint Work

　View Summary

強力な酵素阻害活性を有する天然型（＋）－ノジリマイシン、１-デオキシノジリマイシンとその光学対掌体である（－）- 体をmyo-イノシトールから全合成した．非天然体も強い酵素阻害活性を有することを明らかにした．（10頁）

Formal Total Synthesis of (-)-Isoavenaciolide and (-)-Ethisolide from L-Quebrachitol

千田憲孝、戸部貴彦、諏訪間昌巳、大塚雅己、小川誠一郎

J. Chem. Soc., Perkin Trans. 1  1992.10

Joint Work

　View Summary

L-クェブラキトールの立体選択的官能基化、それに続く環開裂反応により、抗真菌活性を有するビスラクトン、イソアベナシオリド、エチソリドの形式全合成を達成した．（7頁）

Total Synthesis of the Cytotoxic Macrocycle (+)-Hitachimycin

A. B. smith, III, T. A. Rano, N. Chida,G. A.Sulikowski, and J. L. Wood.

J. Am. Chem. Soc. 114  1992.09

Joint Work

　View Summary

抗腫瘍活性を有するマクロラクタム、ヒタチマイシンの全合成に関する詳報．有機亜鉛試薬を用いる３成分連結反応が効果的であることが見いだされた．（15頁）

Total Synthesis and Absolute Configuration of Bengamide A

千田憲孝、戸部貴彦、岡田伸介、小川誠一郎

J. Chem. Soc., Chem. Commun.  1992.08

Joint Work

　View Summary

海産天然物で、新規アミノ酸構造を有するベンガミドＡをL-グルタミン酸、L-クェブラキトールを原料として、初めて全合成し、その絶対構造を確定した．（2頁）

Synthesis and Absolute Configuration of the Naturally Occurring Cyano Glucoside Simmondsin

千田憲孝、山田研、小川誠一郎

J. Chem. Soc., Perkin Trans. 1  1992.05

Joint Work

　View Summary

食物摂取阻害活性を有する天然物、シモンドシンを L-クェブラキトールを出発原料として全合成した．この合成により、本化合物の絶対構造が確定された．（7頁）

Total Synthesis of Antibiotic (-)- Oudemansin X Utilizing L-Quebrachitol as a Chiral Pool

千田憲孝、山田研、小川誠一郎

Chem. Lett.  1992.04

Joint Work

　View Summary

抗真菌性抗生物質である表題化合物を初めて全合成した．L-クェブラキトールの環開裂反応は直鎖状の化合物の合成にも有効にであることが見いだされた．（4頁）

Facile Synthesis of Some L-Sugar Derivatives from L-Quebrachitol

千田憲孝、山田研、鈴木実、小川誠一郎

J. Carbohydr. Chem. 11  1992.03

Joint Work

　View Summary

L-クェブラキトールに位置選択的な環開裂反応を施すことにより、数種類の希少糖を簡便に合成した．（12頁）

Stereoselective Total Synthesis of (+)-Lycoricidine

千田憲孝、大塚雅己、小川誠一郎

Tetrahedron Lett. 32  1991.09

Joint Work

　View Summary

顕著な抗腫瘍活性を示すアルカロイド、リコリシジンをD-グルコースを原料とし、Ferrier 環化反応、パラジウム触媒による骨格形成反応などにより全合成した．（4頁）

Synthesis of Optically Active Substituted Cyclohexenones from Carbohydrates by Catalytic Ferrier Rearrangement

千田憲孝、大塚雅己、雄倉克行、小川誠一郎

Bull. Chem. Soc. Jpn. 64  1991.07

Joint Work

　View Summary

糖質からシクロヘキサノン誘導体を合成するFerrier 反応が中性溶媒中、触媒量の水銀塩で良好に進行することを見いだした．本反応を利用して数種の光学活性多置換シクロヘキセノン類を合成した．（4頁）

Total Synthesis of Antibiotic Hygromycin A

千田憲孝、大塚雅己、中沢圭一、小川誠一郎

J. Org. Chem. 56  1991.04

Joint Work

　View Summary

表題抗生物質をD-グルコースを出発原料とし、Ferrier 環化反応などを利用して、立体選択的に全合成した．本合成により、絶対構造が確定された．（8頁）

Total Synthesis of Simmondsin

千田憲孝、山田研、小川誠一郎

J. Chem. Soc.,Chem. Commun.  1991.04

Joint Work

　View Summary

植物の種子から単離された、食物摂取阻害作用を有する天然物、シモンドシンの初の全合成に関する報告．この合成により絶対構造が確定された．（２頁）

Total Synthesis of Bengamide E

千田憲孝、戸部貴彦、小川誠一郎

Tetrahedron Lett. 32  1991.02

Joint Work

　View Summary

新規な海産天然物であり、興味あるポリヒドロキシ構造を有するベンガミドＥをL-クェブラキトールを原料として初めて全合成し、その絶対構造を確定した．（4頁）

myo-イノシトールを出発原料とした天然型および非天然型ノジリマイシンの合成

千田憲孝、小川誠一郎

ファインケミカル　19  1990.08

Joint Work

　View Summary

未利用資源であるmyo-イノシトールを用いた酵素阻害剤ノジリマイシンの全合成法に関する解説．（7頁）

A Formal Total Synthesis of (-)-Isoavenaciolide from L-Quebrachitol

千田憲孝、戸部貴彦、諏訪間昌巳、大塚雅己、小川誠一郎

J. Chem. Soc.,Chem. Commun.  1990.07

Joint Work

　View Summary

光学活性なシクリトールであるL-クェブラキトールを出発原料とし、立体選択的な炭素-炭素結合の生成、位置選択的な環開裂反応などにより、表題天然物の形式全合成を達成した．（２頁）

Total Synthesis of Methoxyhygromycin and Its 5-Epimer

千田憲孝、中沢圭一、大塚雅己、鈴木実、小川誠一郎

Chem. Lett.  1990.03

Joint Work

　View Summary

抗生物質メトキシハイグロマイシンの初の全合成を達成した．また同時にその５位エピマーも合成し、構造活性相関に関する知見を得た．（４頁）

Total Synthesis of (+)-Hitachimycin

A. B. Smith, III, T. A. Rano, N. Chida, and G. A.Sulikowski

J. Org. Chem. 55  1990.02

Joint Work

　View Summary

大環状ラクタム構造を有する抗腫瘍性物質ヒタチマイシンの初の全合成に関する報告．（２頁）

Conversion of OA-6129B2 into (5R,6R)-6-[(R)-1-Fluoroethyl]7-oxo-3-[(N,N,N'-tri-methylcarbamimidoyl)methyl]thio-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylicacid (88617)

吉岡武男、渡辺東、千田憲孝、深川泰男

J. Antibiot. 42  1989.10

Joint Work

　View Summary

発酵により大量に得られるカルバぺネム系抗生物質、OA-6129B2 をより抗菌力の強い８８６１７物質へ変換する手法を見いだした．（3頁）

New Synthesis of (+)- and (-)-Nojirimycin from myo-Inositol

千田憲孝、古野由佳、小川誠一郎

J. Chem. Soc.,Chem. Commun.  1989.08

Joint Work

　View Summary

抗生物質ノジリマイシンとその光学対掌体をmyo-イノシトールを出発原料として全合成し、それらの酵素阻害活性を検定した．（2頁）

Synthesis of D- and L-Galactose Derivatives from Quebrachitol

千田憲孝、鈴木実、諏訪間昌巳、小川誠一郎

J. Carbohydr. Chem. 8  1989.08

Joint Work

　View Summary

天然ゴム漿液中に大量に含まれている L-クェブラキトールのシクロヘキサン環を位置選択的に開裂させることにより、ガラクトース誘導体へ効率的に変換した．（14頁）

Total Synthesis of Hygromycin A

千田憲孝、大塚雅己、中沢圭一、小川誠一郎

J. Chem. Soc., Chem. Commun.  1989.04

Joint Work

　View Summary

アミノシクリトール系抗生物質、ハイグロマイシンＡをD-グルコースを出発原料として用い、高立体選択的に全合成した．この初の全合成により、絶対構造を決定することができた．（３頁）

Synthesis of Pseudo-trehaloses: [(1,2,4/3,5)-2,3,4-Trihydroxy-5-hydroxymethyl-1-cyclohexyl] D-Gluco-pyranosides

小川誠一郎、横井重喜、木村宣貴、柴田泰史、千田憲孝

Carbohydr. Res. 181  1988.09

Joint Work

　View Summary

トレハロースの環酸素原子を炭素に置換した化合物の誘導体を数種類合成し、核磁気共鳴スペクトルの詳細な検討を行った．（10頁）

Synthesis of Methyl (Methyl D- and L-idopyranosid)uronates from myo-Inositol

千田憲孝、山田絵里子、小川誠一郎

J. Carbohydr. Chem. 7  1988.09

Joint Work

　View Summary

天然に豊富に存在するmyo-イノシトールを出発原料として用い、位置選択的な環開裂反応を利用することによりD- およびL-イズロン酸を合成した．（１６頁）

Synthesis of 2-Acetoxy-4-formyl-phenyl-2,3-di-O-acetyl-6-deoxy-b-D-arabino-5-hexulofuranoside, Structure Confirmation of the Anomeric Configuration of Antibiotic Hygromycin A

千田憲孝、大塚雅己、小川誠一郎

Chem. Lett.  1988.06

Joint Work

　View Summary

アミノシクリトール系抗生物質、ハイグロマイシンＡの糖部分を合成し、アノメリック位の立体配置を決定するとともに、全合成に有用な中間体を合成した．（４頁）

Synthetic Studies on the Validamycins. 10. Total Synthesis of DL-Validoxylamines A and B

小川誠一郎、小川孝生、岩沢善一、豊国達、千田憲孝、須網哲夫．

J. Org. Chem. 49  1984.07

Joint Work

　View Summary

抗生物質バリダマイシンＡの構成成分である表題化合物の初の全合成を達成した．（６頁）

Synthesis and Absolute Configuration of the p-Nitrobenzyl Ester of SQ 27860

宮下正昭、千田憲孝、吉越昭

J. Chem. Soc., Chem. Commun.  1984.03

Joint Work

　View Summary

β－ラクタム系抗生物質である表題化合物をD-グルコサミンより全合成し、未決定であった抗生物質の絶対構造を決定した．（２頁）

Pseudo-sugars. IX. Synthesis of Three (Hydroxymethyl) cyclohexanepentols

小川誠一郎、中村俊信、千田憲孝、須網哲夫

Bull. Chem. Soc. Jpn. 56  1983.05

Joint Work

　View Summary

擬似糖質の誘導体の簡便な合成法の開発に関する報告．（２頁）

Pseudo-sugars. VIII. Synthesis of DL-1-Epivalidamine and Related Compounds

小川誠一郎、大屋雅行、豊国達、千田憲孝、須網哲夫

Bull. Chem. Soc. Jpn. 56  1983.05

Joint Work

　View Summary

抗生物質バリダマイシン類の構成成分であるバリダミンの異性体、ならびに関連化合物の合成報告．（５頁）

Synthetic Studies on the Validamycins. 5.Synthesis of DL-Hydroxyvalidamine and DL-Valienamine

小川誠一郎、千田憲孝、須網哲夫

J. Org. Chem. 48  1983.03

Joint Work

　View Summary

抗生物質バリダマイシンの構成成分であるヒドロキシバリダミンとバリエナミンを共通の中間体から効率的に合成した．（５頁）

Synthetic Studies on the Validamycins. IISynthesis of 1L-1-O-(b-D-Glucopyranosyl)-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol

小川誠一郎、千田憲孝、伊藤裕之、須網哲夫

Bull. Chem. Soc. Jpn. 56  1983.02

Joint Work

　View Summary

表題化合物を合成し、これが天然の抗生物質から得られる化合物と同一であることを確認し、バリダマイシンＡの正しい構造式を提出した．（６頁）

Synthetic Studies on the Validamycins. I. Synthesis of b-D-Glucopyranosylvalidamine: 1L-2-O-(b-D-Glucopyranosyl)-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol

小川誠一郎、柴田靖史、千田憲孝、須網哲夫

Bull. Chem. Soc. Jpn. 56  1983.02

Joint Work

　View Summary

抗生物質バリダマイシンＡの構成成分である表題化合物の推定構造式に対応する化合物を合成したが、天然から得られる標品とは一致しないことを見いだした．（5頁）

Synthesis of the Precursor of (+)-Thienamycin Utilizing D-Glucosamine

宮下正昭、千田憲孝、吉越昭

J. Chem. Soc., Chem. Commun.  1982.12

Joint Work

　View Summary

β-ラクタム系抗生物質チエナマイシンの合成前駆体をD-グルコサミンから光学活性体として合成した．（３頁）

Synthesis of DL-Validoxylamine A

小川誠一郎、小川孝生、千田憲孝、豊国達、須網哲夫

Chem. Lett.  1982.05

Joint Work

　View Summary

抗生物質バリダマイシンＡの分解生成物である表題化合物の初の全合成に関する報告．（４頁）

Synthesis of Hexa-N,O-acetyl-DL-hydroxyvalidamine

小川誠一郎、千田憲孝、須網哲夫

Chem. Lett.  1980.09

Joint Work

　View Summary

抗生物質バリダマイシンＢの構成成分であるヒドロキシバリダミンを初めて合成し、その推定構造式を確定した．（４頁）

Synthesis of 1-O-b-D-Glucopyranosyl-1L-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol. On the Structure of the Antibiotic, Validamycin A

小川誠一郎、千田憲孝、須網哲夫

Chem. Lett.  1980.02

Joint Work

　View Summary

抗生物質バリダマイシンＡの分解生成物の推定構造式の位置異性体を合成したところ、これが標品と一致し、抗生物質の構造式を修正した．（４頁）

Pseudo-sugars. 5. Synthesis of DL-Validatol and DL-Deoxyvalidatol, and Their Epimers

小川誠一郎、豊国達、小俣應二、千田憲孝、須網哲夫

Bull. Chem. Soc. Jpn. 53  1980.02

Joint Work

　View Summary

抗生物質バリダマイシンＡの分解生成物であるバリダトール、デオキシバリダトール、およびそれらのエピマーの合成に関する報告（３頁）

Synthesis of b-D-Glucopyranosyl-validamine: 2-O-b-D-Blucopyranosyl-1L-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol

小川誠一郎、柴田靖史、千田憲孝、須網哲夫

Chem. Lett.  1980.02

Joint Work

　View Summary

抗生物質バリダマイシンＡの分解生成物のひとつである表題化合物を合成したが、標品と一致せず、抗生物質の構造式が不適切であることを指摘した．（４頁）

The Revised Structure of Validamycin A

須網哲夫、小川誠一郎、千田憲孝

J. Antibiot. 33  1980.01

Joint Work

　View Summary

抗生物質バリダマイシンＡの分解生成物の合成から、推定構造式に誤りがあることを見いだし、正しい構造式を提出した（２頁）

Pseudo-sugars. 4. A Facule Synthesis of DL-Validamine and its Derivatives

小川誠一郎、中本浩司、高原雅明、千田憲孝、須網哲夫

Bull. Chem. Soc. Jpn. 52  1979.04

Joint Work

　View Summary

抗生物質バリダマイシン類の構成成分であるバリダミンならびにその誘導体の簡便な合成法の報告（３頁）