Whole-Cell Biotransformation of m-Ethyltoluene into 1S,6R-5-Ethyl-1,6-dihydroxycyclohexa-2,4-diene-1-carboxylic Acid as an Approach to the C-Ring of the Binary Indole–Indoline Alkaloid Vinblastine

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Contents Vol 58(1)

doi:10.1071/CH04185

Whole-Cell Biotransformation of m-Ethyltoluene into 1S,6R-5-Ethyl-1,6-dihydroxycyclohexa-2,4-diene-1-carboxylic Acid as an Approach to the C-Ring of the Binary Indole–Indoline Alkaloid Vinblastine

Martin G. Banwell ^A ^C, Alison J. Edwards ^A, David W. Lupton ^A, Gregg Whited ^B

^A Research School of Chemistry, Institute of Advanced Studies, Australian National University, Canberra ACT 0200, Australia.
^B Genencor International Inc., 925 Page Mill Road, Palo Alto, CA 94304, USA.
^C Corresponding author. Email: mgb@rsc.anu.edu.au





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Australian Journal of Chemistry 58(1) 14–17 http://dx.doi.org/10.1071/CH04185
Submitted: 11 August 2004 Accepted: 11 October 2004 Published online: 14 January 2005

Abstract

The title compound 3, a potential building block for the construction of analogues of the clinically important anti-cancer agent vinblastine (1), has been prepared in an efficient manner through a whole-cell biotransformation of m-ethyltoluene (4) using the microorganism Pseudomonas putida BGXM1 which expresses the enzyme toluate dioxygenase (TADO). Metabolite 3 was readily converted into derivatives 5–8 using conventional chemical techniques and the structure, including absolute stereochemistry, of the last of these was established by single-crystal X-ray analysis.