Abstract
Asymmetric microbial reduction of 2,2-disubstituted-1, 3-cycloalkanediones using common baker’s yeast effected an efficient monoreduction to provide ketol products of high enantiomeric excess. The scope and versatility of this method for a variety of substrates was examined and the integration of selected microbial products in synthetic strategies to various natural products including the trichothecene mycotoxins was illustrated. Yeast reduction of ß-ketoester systems was studied with respect to the effect of remote substituents on the enantioselectivity. Appropriate substrate design provided a useful [R] or [S] 1,3,5-trialkoxypentane synthon of high enantiomeric excess which was applied in synthetic studies of polyene macrolides.
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Brooks, D.W. (1986). Application of Microbial Transformations in the Total Synthesis of Natural Products. In: Schneider, M.P. (eds) Enzymes as Catalysts in Organic Synthesis. NATO ASI Series, vol 178. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-4686-6_9
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