Unified Total Synthesis of (−)-Enigmazole A and (−)-15-O-Methylenigmazole A

Keisuke Sakurai, Keita Sakamoto, Makoto Sasaki, Haruhiko Fuwa

Research output: Contribution to journalArticlepeer-review

Abstract

The total synthesis of cytotoxic marine phosphomacrolides, (−)-enigmazole A and (−)-15-O-methylenigmazole A, is described in detail. The 2,6-cis-substituted tetrahydropyran ring was efficiently elaborated by using a tandem olefin cross-metathesis/intramolecular oxa-Michael addition reaction. The 18-membered macrolactone skeleton was forged via a Au-catalyzed propargylic benzoate rearrangement/macrocyclic ring-closing metathesis sequence. Late-stage diversification of a common intermediate enabled unified total synthesis of (−)-enigmazole A and (−)-15-O-methylenigmazole A.

Original languageEnglish
Pages (from-to)3494-3502
Number of pages9
JournalChemistry - An Asian Journal
Volume15
Issue number21
DOIs
Publication statusPublished - 2020 Nov 2

Keywords

  • gold-catalyzed reaction
  • macrocycles
  • natural products
  • tandem reaction
  • tetrahydropyrans

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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