Novel sequential sigmatropic rearrangements of allylic diols: Application to the total synthesis of ( - )-kainic acid

Katsunori Kitamoto, Mana Sampei, Yasuaki Nakayama, Takaaki Sato, Noritaka Chida

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

Sequential sigmatropic rearrangements (Claisen/Claisen and Claisen/Overman) of enantiopure allylic diols are described. The reactions proceeded in complete diastereoselectivity without protecting group manipulations. The sequential Claisen/Overman rearrangement was successfully applied to the total synthesis of ( - )-kainic acid.

Original languageEnglish
Pages (from-to)5756-5759
Number of pages4
JournalOrganic Letters
Volume12
Issue number24
DOIs
Publication statusPublished - 2010 Dec 17

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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