Stereocontrolled Synthesis of Exocyclic Olefins Using Arene Tricarbonyl Chromium Complex-Catalyzed Hydrogenation. I. Efficient Synthesis of Carbacyclin and Its Analogs

Abstract

An efficient synthesis of carbacyclin and its analogs (2-7) is described in which the stereospecific 1, 4-hydrogenation of a 1, 3-diene to an internal monoene plays a key role. That is, arene·Cr(CO)₃ complex-catalyzed 1, 4-hydrogenation of the dienes 13 and 58, obtainable from the Corey lactone in good yields, under high H₂ pressure afforded the exocyclic olefins 14 and 61 stereospecifically in excellent yields, and these intermediates were converted to therapeutically useful carbacyclin (2) and its analogs 3-7 in a usual way.