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, Scott Stewart, M. Vogtle

Research output: Contribution to journalArticlepeer-review

105 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)223-229
JournalPure and Applied Chemistry
Volume75
Issue number2-3
DOIs
Publication statusPublished - 2003

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