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 0040-4020Full text not available in this repository. (Request a copy from the Strathclyde author)
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.
|Keywords:||pauson–khand reaction, cobalt, stereoselective Wittig reaction, tricyclic sesquiterpene, cedrene, Chemistry, Biochemistry, Organic Chemistry, Drug Discovery|
|Subjects:||Science > Chemistry|
|Department:||Faculty of Science > Pure and Applied Chemistry|
|Depositing user:||Strathprints Administrator|
|Date Deposited:||08 Nov 2011 14:33|
|Last modified:||22 Mar 2017 10:03|