Concise enantioselective synthesis of (+)-aspicilin based on a ruthenium catalyzed olefin metathesis reaction

Toshiko Nishioka, Yoshiharu Iwabuchi, Hiroshi Irie, Susumi Hatakeyama

Research output: Contribution to journalArticlepeer-review

36 Citations (Scopus)

Abstract

An efficient enantioselective synthesis of (+)-aspicilin has been achieved in 12 steps from (2E,5E)-1,7-dibenzyloxy-2,5-heptadiene-4-ol employing Red-Al®-promoted reductive cleavage of the benzyl 4-hydroxy-2- butenyl ether structure and ruthenium catalyzed olefin metathesis as key steps.

Original languageEnglish
Pages (from-to)5597-5600
Number of pages4
JournalTetrahedron Letters
Volume39
Issue number31
DOIs
Publication statusPublished - 1998 Jul 30
Externally publishedYes

Keywords

  • Aspicilin
  • Asymmetric synthesis
  • Olefin metathesis
  • Polyol chiral building block

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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