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.
- pauson–khand reaction
- stereoselective Wittig reaction
- tricyclic sesquiterpene
Kerr, W. J., Crawford, J. J., McLaughlin, M., Pauson, P. L., Morrison, A. J., & 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, 11360-11370. https://doi.org/10.1016/j.tet.2006.05.044