Tetrahedron

Use of a highly effective intramolecular Pauson–Khand cyclisation for the formal total synthesis of (±)-α-and β-cedrene by preparation of cedrone

…, M McLaughlin, AJ Morrison, PL Pauson, GJ Thurston

Index: Crawford, James J.; Kerr, William J.; McLaughlin, Mark; Morrison, Angus J.; Pauson, Peter L.; Thurston, Graeme J. Tetrahedron, 2006 , vol. 62, # 49 p. 11360 - 11370

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Citation Number: 17

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 ...