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Chemoenzymatic Methods for the Enantioselective Preparation of Sesquiterpenoid Natural Products from Aromatic Precursors

Banwell, Martin; Edwards, Alison; Harfoot, Gwion; Jolliffe, Katrina; McLeod, Malcolm; McRae, Kenneth; Stewart, Scott; Vogtle, Markus


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.

CollectionsANU Research Publications
Date published: 2003
Type: Journal article
Source: Pure and Applied Chemistry


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