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Pure Appl. Chem., 2003, Vol. 75, No. 2-3, pp. 223-229

Chemoenzymatic methods for the enantioselective preparation of sesquiterpenoid natural products from aromatic precursors

M. G. Banwell, A. J. Edwards, G. J. Harfoot, K. A. Jolliffe, M. D. McLeod, K. J. McRae, S. G. Stewart and M. Vögtle

Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia

Abstract: The enantiomerically pure cis-1,2-dihydrocatechols 2, which are generated by enzymatic dihydroxylation of the corresponding aromatic, engage in regio- and stereo-controlled Diels-Alder cycloaddition reactions to give a range of synthetically useful bicyclo[2.2.2]octenes. Certain examples of the latter type of compound have been used as starting materials in the synthesis of the sesquiterpenoids (−)-patchoulenone and (−)-hirsutene.