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De Gruyter, Pure and Applied Chemistry, 2-3(75), p. 223-229, 2003

DOI: 10.1351/pac200375020223

Wiley-VCH Verlag, ChemInform, 42(34), 2003

DOI: 10.1002/chin.200342269

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

Journal article published in 2003 by Martin G. Banwell, Markus Vögtle, M. V{̈o}gtle, Alison J. Edwards, Gwion J. Harfoot, Katrina A. Jolliffe ORCID, Malcolm D. McLeod ORCID, Kenneth J. McRae, Scott G. Stewart, Markus Vogtle
This paper is available in a repository.
This paper is available in a repository.

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Abstract

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.