Potent prostacyclin analogs based on the bicyclo [4.2. 0] octane ring system

AF Kluge, DJ Kertesz, C O-Yang…

Index: Kluge, Arthur F.; Kertesz, Denis J.; O-Yang, Counde; Wu, Helen Y. Journal of Organic Chemistry, 1987 , vol. 52, # 13 p. 2860 - 2868

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Citation Number: 31

Abstract

The novel and biologically active prostacyclin mimetics 2 and 29 were prepared in a sequence based on the regioselective opening of epoxide 7 with a lithium acetylide in the presence of boron trifluoride etherate. The regioselectivity of epoxide opening was consistent with a mechanism involving coordination in the transition state of the epoxide and endo acetal oxygens with the Lewis acid boron. Diastereomers 10 and 11 were separated ...

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