論文 - 千田　憲孝

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年

　概要を見る

© 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年

ISSN  14770520

　概要を見る

© 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

千田 憲孝

Journal of the American Chemical Society 139   18386 - 18391 2017年12月

研究論文（学術雑誌）, 査読有り

• Access to Document (DOI)

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

千田 憲孝

Bulletin of the Chemical Society of Japan 90 （ 8 ） 893 - 904 2017年08月

研究論文（学術雑誌）, 共著, 査読有り

• 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

千田 憲孝

Acta Crystallographica, Section E E73   983 - 986 2017年06月

研究論文（学術雑誌）, 共著, 査読有り

• 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年03月

研究論文（学術雑誌）, 共著

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年06月

研究論文（学術雑誌）, 共著, 査読有り

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年06月

研究論文（学術雑誌）, 共著, 査読有り

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年06月

研究論文（学術雑誌）, 共著, 査読有り

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年05月

研究論文（学術雑誌）, 共著, 査読有り

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年05月

研究論文（学術雑誌）, 共著, 査読有り

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年04月

研究論文（学術雑誌）, 共著, 査読有り

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

千田 憲孝

Acta Crystallographica, Section E E72   343 - 346 2016年03月

研究論文（学術雑誌）, 共著, 査読有り

• Access to Document (DOI)

Enantioselective Total Synthesis of (+)-Neostenine

千田 憲孝

Chemistry-A European Journal 22 （ 10 ） 3300 - 3303 2016年03月

研究論文（学術雑誌）, 共著, 査読有り

• Access to Document (DOI)

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

千田 憲孝

Chemistry-An Asian Journal 11 （ 4 ） 470 - 473 2016年02月

研究論文（学術雑誌）, 共著, 査読有り

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

千田 憲孝

Acta Crystallographica, Section E E71   1528 - 1530 2015年12月

研究論文（学術雑誌）, 共著, 査読有り

• Access to Document (DOI)

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

千田 憲孝

Acta Crystallographica, Section E E71   1181 - 1184 2015年10月

研究論文（学術雑誌）, 共著, 査読有り

• Access to Document (DOI)

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

千田 憲孝

Organic Letters 17 （ 11 ） 2574 - 2577 2015年06月

研究論文（学術雑誌）, 共著, 査読有り

• Access to Document (DOI)

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

千田 憲孝

Organic Letters 17 （ 11 ） 2570 - 2573 2015年06月

研究論文（学術雑誌）, 共著, 査読有り

• 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

千田 憲孝

Acta Crystallographica, Section E E71   490 - 493 2015年04月

研究論文（学術雑誌）, 共著, 査読有り

• Access to Document (DOI)