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

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

研究成果: Article査読

26 被引用数 (Scopus)

抄録

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.

本文言語English
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
4
DOI
出版ステータスPublished - 2015

ASJC Scopus subject areas

  • 化学 (全般)

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