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. V�gtle
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.
*Pure Appl.Chem. 75,
141�419 (2003). An issue of reviews and research papers based on
lectures presented at the 23rd IUPAC International Symposium on the
Chemistry of Natural Products, Florence, Italy, 28 July � 2 August 2002.
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