Stereoselective microbial reduction process

Details Stereoselective microbial reduction process Stereoselective microbial reduction process

C - Chemistry, Metallurgy

12

P

C12P 17/14 (2006.01) C12P 7/42 (2006.01)

Patent

CA 2231808

A stereoselective reduction of compound of formula II to compound of formula I, which comprises adding compound of formula II to a culture broth of the Zygosaccharomyces bailii ATCC 38924, incubating the resulting mixture, and isolating a hydroxy compound of formula I, is described. A stereoselective reduction of a compound of formula IV to compound of formula III, which comprises adding a compound of formula IV to a culture broth of Schizosaccharomyces octosporus ATCC 2479, incubating the resulting mixture, and isolating a hydroxy compound of formula III is also described. The resulting compounds of formula I and III are useful as intermediates in the preparation of 1-(4-fluorophenyl)-3(R) -[3(S)-hydroxy-3-(4- fluorophenyl)propyl)]-4(S)-(4-hydroxyphenyl)-2-azetidionone which is a serum cholesterol lowering agent.

L'invention porte sur la réduction stéréosélective du composé de formule (II) donnant le composé de formule (I), laquelle consiste à ajouter le composé de formule (II) à un bouillon de culture de Zygosaccharomyces bailii ATCC 38924, à incuber le mélange résultant, et à isoler le composé hydroxy de formule (I). L'invention porte également sur la réduction stéréosélective du composé de formule (IV) donnant le composé de formule (III), laquelle consiste à ajouter le composé de formule (IV) à un bouillon de culture de Schizosaccharomyces octosporus ATCC 2479, à incuber le mélange résultant, et à isoler le composé hydroxy de formule (III). Les composés résultants de formule (I) et (III) servent d'intermédiaires dans la préparation du 1-(4-fluorophényl)-3(R)-[3(S)-hydroxy-3-(4-fluorophényl)propyl)]-4(S)-(4-hydroxyphényl)-2-azétidinone, agent qui abaisse la teneur en cholestérol du sérum.

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