Enantioselective preparation of 1-benzyloxy-3-methyl-6-heptene-2,4-diols: Total synthesis of (+)-prelactone C

Tomoyuki Esumi, Hiroko Fukuyama, Reiko Oribe, Kaori Kawazoe, Yoshiharu Iwabuchi, Hiroshi Irie, Susumi Hatakeyama

Research output: Contribution to journalArticlepeer-review

23 Citations (Scopus)

Abstract

A concise method leading to all stereoisomers of 1-benzyloxy-3-methyl-6-heptene-2,4-diol from (2E,5E)-1,7-dibenzyloxy-2,5-heptadiene-4-ol has been developed. The first synthesis of (+)-prelactone C, a δ-lactone isolated from the concanamycin-producing Streptomyces sp., has been achieved utilizing (2S,3S,4R)-1-benzyloxy-3-methyl-6-heptene-2,4-diol as a chiral building block.

Original languageEnglish
Pages (from-to)4823-4826
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number27
DOIs
Publication statusPublished - 1997 Jul 7
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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