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 journalArticle

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

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Cycloaddition
Cycloaddition Reaction
cycloaddition
biosynthesis
Biosynthesis
synthesis
diagrams
rubifolide
isoepilophodione B
bipinnatin J
intricarene

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Exploring biosynthetic relationships among furanocembranoids : Synthesis of (-)-bipinnatin J, (H-)-intricarene, (+)-rubifolide, and (+)-isoepilophodione B. / Roethle, Paul A.; Hernandez, Paul T.; Trauner, Dirk.

In: Organic Letters, Vol. 8, No. 25, 07.12.2006, p. 5901-5904.

Research output: Contribution to journalArticle

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