Total Synthesis of (−)-Enigmazole A

Keisuke Sakurai, Makoto Sasaki, Haruhiko Fuwa

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

Total synthesis of (−)-enigmazole A, a marine macrolide natural product with cytotoxic activity, has been accomplished. The tetrahydropyran moiety was constructed by means of a domino olefin cross-metathesis/intramolecular oxa-Michael addition of a δ-hydroxy olefin. After coupling of advanced intermediates, the macrocycle was formed through gold-catalyzed rearrangement of a propargylic benzoate, followed by ring-closing metathesis of the resultant α,β-unsaturated ketone.

Original languageEnglish
Pages (from-to)5143-5146
Number of pages4
JournalAngewandte Chemie - International Edition
Volume57
Issue number18
DOIs
Publication statusPublished - 2018 Apr 23
Externally publishedYes

Keywords

  • macrocycles
  • metathesis
  • natural products
  • rearrangement
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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