The total synthesis of (-)-crispatene

Aubry K. Miller, Daniel H. Byun, Christopher M. Beaudry, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

The total synthesis of the molluscan polypropionate (-)-crispatene is described. The synthesis features a palladium-catalyzed cross-coupling to establish a sensitive conjugated tetraene and its Lewis acid-catalyzed cycloisomerization to yield the bicyclo[3.1.0]hexene core of the natural product. The absolute configuration of (-)-crispatene and related molecules is established.

Original languageEnglish (US)
Pages (from-to)12019-12023
Number of pages5
JournalProceedings of the National Academy of Sciences of the United States of America
Volume101
Issue number33
DOIs
StatePublished - Aug 17 2004

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Lewis Acids
Palladium
Biological Products
crispatene
1-hexene

ASJC Scopus subject areas

  • Genetics
  • General

Cite this

The total synthesis of (-)-crispatene. / Miller, Aubry K.; Byun, Daniel H.; Beaudry, Christopher M.; Trauner, Dirk.

In: Proceedings of the National Academy of Sciences of the United States of America, Vol. 101, No. 33, 17.08.2004, p. 12019-12023.

Research output: Contribution to journalArticle

Miller, Aubry K. ; Byun, Daniel H. ; Beaudry, Christopher M. ; Trauner, Dirk. / The total synthesis of (-)-crispatene. In: Proceedings of the National Academy of Sciences of the United States of America. 2004 ; Vol. 101, No. 33. pp. 12019-12023.
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