Use of a highly effective intramolecular Pauson-Khand cyclisation for the formal total synthesis of (+/-) alpha- and beta- cedrene by preparation of cedrone

W.J. Kerr, J.J. Crawford, M. McLaughlin, P.L. Pauson, A.J. Morrison, G.J. Thurston

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

The cedrene carbon skeleton was directly and efficiently assembled from a simple monocyclic precursor by the strategic use of a high yielding intramolecular Pauson–Khand cyclisation reaction. A small number of further synthetic manipulations provided a concise formal total synthesis of α- and β-cedrene. The cyclisation precursor was readily prepared, with a stereoselective ketone alkenylation selectively providing the olefin required for efficient access to the natural target.

Original languageEnglish
Pages (from-to)11360-11370
Number of pages10
JournalTetrahedron
Volume62
DOIs
Publication statusPublished - 2006

Keywords

  • pauson–khand reaction
  • cobalt
  • stereoselective Wittig reaction
  • tricyclic sesquiterpene
  • cedrene

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