From Toluene to TaxolTM: Chemoenzymatic and Enantiodivergent Routes to the AB-Ring Systems of Taxoids and ent-Taxoids

Martin G. Banwell; Penny Darmos; Malcolm D. McLeod; David C. R. Hockless

doi:10.1055/s-1998-1801

Synlett 1998; 1998(8): 897-899
DOI: 10.1055/s-1998-1801

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From Toluene to Taxol^TM: Chemoenzymatic and Enantiodivergent Routes to the AB-Ring Systems of Taxoids and ent-Taxoids

Martin G. Banwell^* , Penny Darmos, Malcolm D. McLeod, David C. R. Hockless

^*Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia; Fax 61-2-6249-5995; E-mail: mgb@rsc.anu.edu.au

Abstract

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The cis-1,2-dihydrocatechol 2 has been converted, via reaction sequences including Diels-Alder cycloaddition and anionic oxy-Cope rearrangement steps, into the enantiopure bicyclo[5.3.1]undecanes 20 and 33 which correspond to the AB-ring systems of ent-taxoids and taxoids, respectively.

anionic oxy-Cope rearrangement - Diels-Alder cycloaddition - cis-1,2-dihydrocatechol - enantiodivergent synthesis - taxoids

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