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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Rapid, Chemoenzymatic Syntheses of the Epoxyquinols (–)-Bromoxone Acetate and (–)-Tricholomenyn A

David M. Pinkerton A , Martin G. Banwell A B and Anthony C. Willis A
+ Author Affiliations
- Author Affiliations

A Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia.

B Corresponding author. Email: mgb@rsc.anu.edu.au

Australian Journal of Chemistry 62(12) 1639-1645 https://doi.org/10.1071/CH09469
Submitted: 7 September 2009  Accepted: 20 October 2009   Published: 10 December 2009

Abstract

The epoxyquinol derivatives (–)-bromoxone acetate (ent-1) and (–)-tricholomenyn A (2) have been prepared from the cis-1,2-dihydrocatechols 3 and 4, respectively. Compounds 3 and 4 are themselves obtained in enantiomerically pure form through the whole-cell biotransformation of the corresponding halobenzene.


Acknowledgements

We thank the Institute of Advanced Studies and the Australian Research Council for financial support.


References


[1]   T. Higa, R. K. Okuda, R. M. Severns, P. J. Scheuer, C.-H. He, X. Changfu, J. Clardy, Tetrahedron 1987, 43,  1063.
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        | Crossref |  GoogleScholarGoogle Scholar | CAS |  (accessed September 7, 2009). (a) For reviews on methods for generating cis-1,2-dihydrocatechols by microbial dihydroxylation of the corresponding aromatics, as well as the synthetic applications of these metabolites, see: Hudlicky T. , Gonzalez D. , Gibson D. T. , Aldrichimica Acta 1999, 32, 35.
       (b) M. G. Banwell, A. J. Edwards, G. J. Harfoot, K. A. Jolliffe, M. D. McLeod, K. J. McRae, S. G. Stewart, M. Vögtle, Pure. Appl. Chem. 2003, 75,  223.
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