Total Synthesis and Structure Revision of (-)-Siphonodictyal B and Its Biomimetic Conversion into (+)-Liphagal

Adrian W. Markwell-Heys, Kevin Kuan, Jonathan H. George

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

The structure of siphonodictyal B has been reassigned on the basis of the total synthesis of both possible C-8 epimers. The revised structure of siphonodictyal B was converted into liphagal by acid catalyzed rearrangement of a proposed epoxide intermediate. This biomimetic cascade features a succession of four distinct reactions (epoxidation, o-quinone methide formation, ring expansion, and benzofuran formation) that occur in a one-pot operation under mild conditions. During these studies we also isolated a surprisingly stable o-quinone methide that supports our mechanistic proposal for liphagal biosynthesis.

Original languageEnglish
Pages (from-to)4228-4231
Number of pages4
JournalOrganic Letters
Volume17
Issue number17
DOIs
Publication statusPublished - 21 Aug 2015

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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