Total synthesis of (±)-gephyrotoxin by amide-selective reductive nucleophilic addition

Kenji Shirokane, Takamasa Wada, Makoto Yoritate, Ryo Minamikawa, Nobuaki Takayama, Takaaki Sato, Noritaka Chida

研究成果: Contribution to journalArticle査読

95 被引用数 (Scopus)

抄録

A chemoselective approach for the total synthesis of (±)- gephyrotoxin has been developed. The key to success was the utilization of N-methoxyamides, which enabled the direct coupling of the amide with an aldehyde and selective reductive nucleophilic addition to the amide in the presence of a variety of sensitive and electrophilic functional groups, such as a methyl ester. This chemoselective approach minimized the use of protecting-group manipulations and redox reactions, which resulted in the most concise and efficient total synthesis of (±)-gephyrotoxin described to date. Aim for selectivity: A chemoselective approach that utilizes N-methoxyamides has been developed for the total synthesis of (±)-gephyrotoxin. The N-methoxy group enabled the direct coupling of the amide with an aldehyde and amide-selective reductive allylation in the presence of a more electrophilic methyl ester, which resulted in the most concise and efficient total synthesis of (±)-gephyrotoxin described to date.

本文言語英語
ページ(範囲)512-516
ページ数5
ジャーナルAngewandte Chemie - International Edition
53
2
DOI
出版ステータス出版済み - 1 7 2014
外部発表はい

All Science Journal Classification (ASJC) codes

  • 触媒
  • 化学 (全般)

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