A biomimetic total synthesis of (+)-intricarene

Bencan Tang, Christopher D. Bray, Gerald Pattenden

Research output: Journal PublicationArticlepeer-review

78 Citations (Scopus)

Abstract

An asymmetric synthesis of the furanocembrane (-)-bipinnatin J (3a) found in gorgonian corals is described. Treatment of 3a with VO(acac)2-tBuOOH, followed by acetylation, gave acetoxypyranone 15. When 15 was heated in the presence of DBU, it underwent a transannular oxidopyrylium-alkene [5+2] cycloaddition producing the polycyclic diterpene (+)-intricarene 1, isolated from the coral Pseudopterogorgia kallos. The total synthesis of intricarene 1 mimics its most likely biosynthesis via oxidation of bipinnatin J (3a) in vivo.

Original languageEnglish
Pages (from-to)6401-6404
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number36
DOIs
Publication statusPublished - 4 Sep 2006
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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