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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. and Crawford, J.J. and McLaughlin, M. and Pauson, P.L. and Morrison, A.J. and Thurston, G.J. (2006) Use of a highly effective intramolecular Pauson-Khand cyclisation for the formal total synthesis of (+/-) alpha- and beta- cedrene by preparation of cedrone. Tetrahedron, 62. pp. 11360-11370. ISSN 0040-4020

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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.