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

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Date

2003

Authors

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

Journal Title

Journal ISSN

Volume Title

Publisher

International Union of Pure and Applied Chemistry

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.

Description

Keywords

Keywords: alkene derivative; catechol derivative; hirsutene; sesquiterpenoid; conference paper; cycloaddition; Diels Alder reaction; dihydroxylation; enantiomer; priority journal; stereochemistry; synthesis; technique

Citation

URI

http://hdl.handle.net/1885/85830

Collections

ANU Research Publications

Source

Pure and Applied Chemistry

Type

Journal article

Book Title

Entity type

Access Statement

License Rights

DOI

Restricted until

2037-12-31

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