Exploring biosynthetic relationships among furanocembranoids: Synthesis of (-)-bipinnatin J, (H-)-intricarene, (+)-rubifolide, and (+)-isoepilophodione B

Paul A. Roethle, Paul T. Hernandez, Dirk Trauner

Research output: Contribution to journalArticlepeer-review

Abstract

(Diagram presented) The asymmetric total synthesis of (-)-bipinnatin J and its conversion into (+)-intricarene through a transannular 1,3-dipolar cycloaddition is described. In addition, the conversion of (-)-bipinnatin J into (+)-rubifolide and (+)-isoepilophodione B is reported. Biosynthetic relationships among furanocembranoids and the possible role of 1,3-dipolar cycloadditions in biosynthesis are discussed.

Original languageEnglish (US)
Pages (from-to)5901-5904
Number of pages4
JournalOrganic Letters
Volume8
Issue number25
DOIs
StatePublished - Dec 7 2006

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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