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Bakers' yeast (Saccharomyces cerevisiae) mediated reductions were investigated for the potential of a fermentation approach towards novel paclitaxel C-13 side-chain analogs bearing a polar methoxy-functionality in combination with a rigid structural core unit. Synthesis of correspondingly substituted α-keto-β-lactam compounds as biotransformation precursors was carried out following a straightforward strategy involving Staudinger (2+2) cyclization. Bioreductions were carried out using growing whole-cells of S. cerevisiae and the dia- and enantioselectivity of the process was studied.

Synthesis and yeast mediated bioreduction of α-keto-β-lactams bearing a functionalized and rigid side chain