Taxanes have been of interest to both chemistry and biology for nearly 50 years. This enduring interest has been in part due to their molecular complexity and significant biological activity. While synthetic biology has met the demand for Taxol© (1).1 Accessing other lower to medium oxidation level taxanes (Taxinine 2 and Taxusin 3) is still a challenge. We envisaged using both synthetic biology and synthetic chemistry to produce a wide range of taxanes. Central to this approach is 5-α-hydroxytaxadiene 5. Here we show that 5 can be accessed by both synthetic biology, utilising taxadiene 7 extracted from metabolically engineered tomato fruit2 and by synthetic chemistry using farnesol 4 as starting material. Work is now ongoing to oxidise 5 further to obtain medium oxidation level taxanes. 1. O. Expósito and M. Bonfill, Anticancer. Agents Med. Chem., 2009, 9, 109–121. 2. K. Kovacs, L. Zhang, R. S. T. Linforth, B. Whittaker, C. J. Hayes, and R. G. Fray, Transgenic Res., 2007, 16, 121–126.

Synthetic chemistry and synthetic biology: The bottom-up approach to taxane synthesis

251st National Meeting (2016)

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