Biomimetic synthesis of the shimalactones

Vladimir Sofiyev, Gabriel Navarro, Dirk Trauner

Research output: Contribution to journalArticlepeer-review

Abstract

A biomimetic synthesis of shimalactone A and B is described. Its key features are an unprecedented acid-catalyzed cyclization of a dienyl β-ketolactone and a Stille coupling/8π-6π electrocyclization cascade to create the oxabicyclo[2.2.1]heptane and bicyclo[4.2.0]octadiene, respectively. The synthesis is convergent and void of protecting groups.

Original languageEnglish (US)
Pages (from-to)149-152
Number of pages4
JournalOrganic Letters
Volume10
Issue number1
DOIs
StatePublished - Jan 3 2008

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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