TRIPLY-CONVERGENT SYNTHESIS OF A HOMOCHIRAL 3,3-DIMETHYL, 15-CYCLOHEXYL PROSTACYCLIN ANALOG

被引:10
作者
BERGLUND, RA [1 ]
BRAISH, TF [1 ]
JAKUBOWSKI, JA [1 ]
FUCHS, PL [1 ]
机构
[1] ELI LILLY & CO,DEPT CARDIOVASC PHARMACOL,INDIANAPOLIS,IN 46285
关键词
D O I
10.1016/S0960-894X(01)81170-7
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Allylic bromocuprate reagent 13b undergoes synfacial SN2' addition to homochiral allyl ammonium salt 14 to provide vinyl sulfone 15 as a single stereoisomer. Addition of homochiral acetylenic anion 18 to vinyl sulfone 17 smoothly provides the bicyclic sulfone 19 which is further transformed to prostacyclin analog 22. Analog 22 was only a weak inhibitor of platelet aggregation having an IC50 of 0.48-mu-M.
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页码:649 / &
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