Stereoselective synthesis of both enantiomers of ketoconazole from (R)-and (S)-epichlorohydrin

P Camps, X Farrés, ML García, J Ginesta…

Index: Camps, Pelayo; Farres, Xavier; Garcia, Luisa; Ginesta, Joan; Pascual, Jaume; et al. Tetrahedron: Asymmetry, 1995 , vol. 6, # 6 p. 1283 - 1294

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Citation Number: 23

Abstract

Stereoselective syntheses of both enantiomers of ketoconazole (1) from commercially available (R)-or (S)-epichlorohydrin has been developed. The key-step of these syntheses involves the selective substitution of the methylene chlorine atom by benzoate on a mixture of (2S, 4R)-14a and (2R, 4R)-15a or of their enantiomers, followed by crystallization of the corresponding cis-benzoates,(2S, 4R)-18 or (2S, 4S)-18, from which (+)-or (−)-1 were ...