SYNTHESIS OF ARTIFICIAL HMG-COA REDUCTASE INHIBITORS BASED ON THE OLEFINATION STRATEGY

被引:33
作者
HIYAMA, T [1 ]
MINAMI, T [1 ]
TAKAHASHI, K [1 ]
机构
[1] TOKYO INST TECHNOL, RESOURCES UTILIZAT RES LAB, MIDORI KU, YOKOHAMA, KANAGAWA 226, JAPAN
关键词
D O I
10.1246/bcsj.68.364
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Synthetic methods were studied for optically active 6-oxo-3,5-isopropylidenedioxyhexanoate esters (4), which could be used as a key precursor of various kinds of artificial analogs of 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitors. An enantiomer (+)-4 was prepared by asymmetric reduction of beta,delta-diketo esters derived from the Taber's alcohol or L-tartrate followed by a series of chemical transformations, and the desired enantiomer (-)-4 was prepared by the same asymmetric reduction starting from D-tartrate. The key intermediate (-)-4 was finally converted into a highly potent HMG-CoA reductase inhibitor, NK-104.
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收藏
页码:364 / 372
页数:9
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