Baker's yeast-mediated reductions of α-keto esters and an α-keto-β-lactam. Two routes to the paclitaxel side chain

MM Kayser, MD Mihovilovic, J Kearns…

Index: Kayser, Margaret M.; Mihovilovic, Marko D.; Kearns, Jeff; Feicht, Anton; Stewart, Jon D. Journal of Organic Chemistry, 1999 , vol. 64, # 18 p. 6603 - 6608

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Citation Number: 63

Abstract

Baker's yeast (Saccharomyces cerevisiae) has been used to reduce a series of alkyl esters derived from pyruvate and benzoylformate. Both the yield and enantioselectivities of these reductions were maximized when methyl esters were used, and the (R)-alcohols were isolated in all instances. Yeast-mediated ester hydrolysis was a significant side reaction for products derived from long-chain alcohols. In the case of ethyl benzoylformate, the ...