Total Synthesis of (–)-Stemoamide by Sequential Overman/Claisen Rearrangement

Yasuaki Nakayama, Yuichiro Maeda, Naoto Hama, Takaaki Satou, Noritaka Chida

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The enantioselective total synthesis of (–)-stemoamide using Overman/Claisen rearrangement of an allylic 1,2-diol is reported. The enantiopure allylic 1,2-diol was efficiently prepared from naturally occurring dimethyl tartrate. The chirality transfer reactions through two consecutive [3,3]-sigmatropic rearrangements proceeded with complete diastereoselectivity in a one-pot process.

Original languageEnglish
JournalSynthesis (Germany)
DOIs
Publication statusAccepted/In press - 2016 Feb 23

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Keywords

  • alkaloid
  • allylic compound
  • diol
  • sigmatropic rearrangement
  • total synthesis

ASJC Scopus subject areas

  • Organic Chemistry
  • Catalysis

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