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.

LanguageEnglish
Pages11360-11370
Number of pages10
JournalTetrahedron
Volume62
DOIs
Publication statusPublished - 2006

Fingerprint

Cyclization
Alkenylation
Alkenes
Ketones
Skeleton
Carbon
cedrene

Keywords

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

Cite this

Kerr, W.J. ; Crawford, J.J. ; McLaughlin, M. ; Pauson, P.L. ; Morrison, A.J. ; Thurston, G.J. / Use of a highly effective intramolecular Pauson-Khand cyclisation for the formal total synthesis of (+/-) alpha- and beta- cedrene by preparation of cedrone. In: Tetrahedron. 2006 ; Vol. 62. pp. 11360-11370.
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Use of a highly effective intramolecular Pauson-Khand cyclisation for the formal total synthesis of (+/-) alpha- and beta- cedrene by preparation of cedrone. / Kerr, W.J.; Crawford, J.J.; McLaughlin, M.; Pauson, P.L.; Morrison, A.J.; Thurston, G.J.

In: Tetrahedron, Vol. 62, 2006, p. 11360-11370.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Use of a highly effective intramolecular Pauson-Khand cyclisation for the formal total synthesis of (+/-) alpha- and beta- cedrene by preparation of cedrone

AU - Kerr, W.J.

AU - Crawford, J.J.

AU - McLaughlin, M.

AU - Pauson, P.L.

AU - Morrison, A.J.

AU - Thurston, G.J.

PY - 2006

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KW - pauson–khand reaction

KW - cobalt

KW - stereoselective Wittig reaction

KW - tricyclic sesquiterpene

KW - cedrene

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