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 and Gregg Whited BA 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
Australian Journal of Chemistry 58(1) 14-17 https://doi.org/10.1071/CH04185
Submitted: 11 August 2004 Accepted: 11 October 2004 Published: 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.
Acknowledgments
We thank the Institute of Advanced Studies as well as the Australian Research Council Discovery Program for generous financial support.
[1]
[2]
For an up to date minireview on synthetic studies in the area, see: C. Schneider,
Angew. Chem. Int. Ed. 2002, 41, 4217.
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[15]
