A concise synthesis of pinellic acid using a cross-metathesis approach

Ayako Miura, Shigefumi Kuwahara

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

A new enantioselective synthesis of pinellic acid, a trihydroxy unsaturated fatty acid exhibiting oral adjuvant activity for nasally administered influenza vaccine, has been accomplished using a cross-metathesis reaction between two terminal olefin intermediates as the key step. This synthesis is the shortest to date, furnishing pinellic acid in 17% overall yield via only seven steps from a readily available known dihydroxy ester.

Original languageEnglish
Pages (from-to)3364-3368
Number of pages5
JournalTetrahedron
Volume65
Issue number17
DOIs
Publication statusPublished - 2009 Apr 25

Keywords

  • Cross-metathesis
  • Fatty acid
  • Influenza
  • Pinellic acid
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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