Papers - Chida, Noritaka

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

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© 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).

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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

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© 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.

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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