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

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

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)522-537
Number of pages16
JournalBulletin of the Chemical Society of Japan
Volume88
Issue number4
DOIs
Publication statusPublished - Jan 1 2015

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Allylation
Amides
Redox reactions
Aldehydes
gephyrotoxin

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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Total syntheses of (±)-gephyrotoxin and (±)-perhydrogephyrotoxin. / Shirokane, Kenji; Tanaka, Yuya; Yoritate, Makoto; Takayama, Nobuaki; Sato, Takaaki; Chida, Noritaka.

In: Bulletin of the Chemical Society of Japan, Vol. 88, No. 4, 01.01.2015, p. 522-537.

Research output: Contribution to journalArticle

Shirokane, Kenji ; Tanaka, Yuya ; Yoritate, Makoto ; Takayama, Nobuaki ; Sato, Takaaki ; Chida, Noritaka. / Total syntheses of (±)-gephyrotoxin and (±)-perhydrogephyrotoxin. In: Bulletin of the Chemical Society of Japan. 2015 ; Vol. 88, No. 4. pp. 522-537.
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