… synthesis of carba-prostacyclin analogues based on organocopper conjugate addition to a bicyclic azoene and its application to the synthesis of 13, 14-dinor-inter-p- …

M van Bergen, HJ Gais

Index: Van Bergen, Marc; Gais, Hans-Joachim Journal of the American Chemical Society, 2002 , vol. 124, # 16 p. 4321 - 4328

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Citation Number: 18

Abstract

An enantioselective synthesis of E/Z-13, 14-dinor-inter-p-phenylene carbacyclin (E/Z-2d) by a new strategy has been realized that holds the prospect of serving as a general route for carba-prostacyclin analogues. The key intermediate in this synthesis is the bicyclic azoene Ts-9, and the key step is the regio-and stereoselective conjugate addition of the chiral arylcopper compound Cu-8d/Pn-Bu3 to the azoene with formation of hydrazone 7d. ...