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Chemo-enzymatic synthesis of (R)-(+)-aminoglutethimide by kinetic resolution of (±)-4-cyano-4-phenyl-1-hexanol |
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| Authors: | Dai Sig Im Chan Seong Cheong So Ha Lee Youn Kyoung Jung In Howa Jeong |
| Affiliation: | a Life Sciences Division, Korea Institute of Science and Technology, P.O. Box 131, Cheongryang, Seoul 130-650, South Korea b Computer-Aided Molecular Design and Bioscience Research Co., Ltd., 464-5 Jung-ri, Kusong-myon, Yongin-shi, Kyonggi-do 449-916, South Korea c Department of Chemistry, Yonsei University, Wonju 220-710, South Korea |
| Abstract: | Chemo-enzymatic approaches for the synthesis of the family of aromatase inhibitory drug via lipase-catalyzed kinetic resolution of (±)-4-cyano-4-phenyl-1-hexanol (2) as appropriate precursors were described. Enzymatic transesterification of primary alcohol (±)-2 using Pseudomonas cepacia (Amano PS, PCL) provided the enantiopure alcohol (R)-(−)-2 with 99% ee at conversion of 86%, while that of (±)-2 using Pseudomonas fluorescens (Amano AK, LAK) provided the (S)-(+)-2 with 96% ee at conversion of 86%. Chemical transformation of substrate (R)-(−)-2 gave (R)-(+)-aminoglutethimide (1) in enantioselectively high yield. |
| Keywords: | Aminoglutethimide Tertiary benzylic center Enzymatic resolution Transesterification Enantioselective |
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