Total syntheses of (±)-gephyrotoxin and (±)-perhydrogephyrotoxin

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

研究成果: Contribution to journalArticle

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This article describes the full details of our total syntheses of gephyrotoxin and perhydrogephyrotoxin. Our central strategy toward the total synthesis is based on the use of an N-methoxy group as a reactivity control element. The N-methoxyamide group enabled unique transformations, involving i) the direct coupling reaction of the N-methoxyamide with an aldehyde, and ii) the amide-selective reductive allylation. These reactions were never accomplished without the assistance of the N-methoxy group. The amide-selective reductive allylation of the N-methoxyamide was especially practical, and excluded a number of extra steps including protecting group manipulations and redox reactions in the total syntheses.

元の言語英語
ページ(範囲)522-537
ページ数16
ジャーナルBulletin of the Chemical Society of Japan
88
発行部数4
DOI
出版物ステータス出版済み - 1 1 2015
外部発表Yes

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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