Issue 22, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

A chemoenzymatic synthesis of (−)-hirsutene from toluene

Martin G. Banwell,*a   Alison J. Edwards,a   Gwion J. Harfoota  and  Katrina A. Jolliffea  

* Corresponding authors

a Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia
E-mail: mgb@rsc.anu.edu.au

Abstract

The enantiomerically pure cis-1,2-diol 2, which is obtained by microbial oxidation of toluene, has been converted, via a sequence of reactions including high-pressure promoted Diels–Alder cycloaddition and oxa-di-π-methane rearrangement steps, into the triquinane (−)-hirsutene (1).

Graphical abstract: A chemoenzymatic synthesis of (−)-hirsutene from toluene

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Article information

DOI
https://doi.org/10.1039/B208778B
Article type
Communication
Submitted
12 Sep 2002
Accepted
18 Oct 2002
First published
28 Oct 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 2439-2441

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A chemoenzymatic synthesis of (−)-hirsutene from toluene

M. G. Banwell, A. J. Edwards, G. J. Harfoot and K. A. Jolliffe, J. Chem. Soc., Perkin Trans. 1, 2002, 2439 DOI: 10.1039/B208778B

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