STEREOSELECTIVE SYNTHESES OF BOTH ENANTIOMERS OF KETOCONAZOLE FROM (R)-EPICHLOROHYDRIN AND (S)-EPICHLOROHYDRIN

被引：20

作者：

CAMPS, P ^{[1
]}

FARRES, X ^{[1
]}

GARCIA, ML ^{[1
]}

GINESTA, J ^{[1
]}

PASCUAL, J ^{[1
]}

MAULEON, D ^{[1
]}

CARGANICO, G ^{[1
]}

机构：

[1] LABS MENARINI SA,DEPT I & D,E-08912 BADALONA,SPAIN

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 06期

关键词：

D O I：

10.1016/0957-4166(95)00161-H

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

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, (2R,4R)-18 or (2S,4S)-18, from which (+)- or (-)-1 were obtained as described for (+/-)-1. The ee's of (+) and (-)-ketoconazole were determined by HPLC on the CSP Chiralcel OD-H.

引用

页码：1283 / 1294

页数：12

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