A Highly Convergent and Biomimetic Total Synthesis of Portentol

Bichu Cheng, Dirk Trauner

Research output: Contribution to journalArticlepeer-review

Abstract

An efficient total synthesis of the unusual polyketide portentol is reported. Three boron aldol reactions were used to assemble the linear carbon chain of the natural product, which contains two challenging anti-anti stereotriads. A biomimetic double cyclization cascade, triggered by an oxidation, then afforded portentol and its known dehydration product, anhydroportentol. The biosynthesis of portentol and the biosynthetic relevance of our key step are discussed.

Original languageEnglish (US)
Pages (from-to)13800-13803
Number of pages4
JournalJournal of the American Chemical Society
Volume137
Issue number43
DOIs
StatePublished - Nov 4 2015

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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