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

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

Research output: Contribution to journalArticlepeer-review

15 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
Article numberss-2016-c0050-st
Pages (from-to)1647-1654
Number of pages8
JournalSynthesis (Germany)
Volume48
Issue number11
DOIs
Publication statusPublished - 2016 Jun 2

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Total Synthesis of (-)-Stemoamide by Sequential Overman/Claisen Rearrangement'. Together they form a unique fingerprint.

Cite this