Cross-metathesis approach to a (2E,4E)-dienoic acid intermediate for the synthesis of elaiolide

Akira Morita, Shigefumi Kuwahara

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)

Abstract

A (2E,4E)-7-hydroxy-2,4-dienoic acid, previously employed as a key intermediate for the total synthesis of the macrodiolide antibiotic elaiolide, was prepared stereoselectively and concisely from (S)-2-methyl-3-trityloxypropanal by a three-step sequence consisting of Brown's asymmetric crotylboration, olefin cross-metathesis, and alkaline treatment. Ethyl 3-pivaloyloxy-4-pentenoate was used as a masked dienoate in the cross-metathesis step.

Original languageEnglish
Pages (from-to)3163-3166
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number18
DOIs
Publication statusPublished - 2007 Apr 30

Keywords

  • 2,4-Alkadienoic acid
  • Antibiotic
  • Cross-metathesis
  • Elaiolide
  • Enantioselective synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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