A CATALYTIC ASYMMETRIC-SYNTHESIS OF 11-DEOXY-PGF(1-ALPHA), USING ALB,A HETEROBIMETALLIC MULTIFUNCTIONAL ASYMMETRIC COMPLEX

A catalytic asymmetric synthesis of 11-deoxy-PGF(1 alpha) has been ach ieved using a cascade Michael-aldol reaction as a key step. This casca de reaction was efficiently promoted by a catalytic use of AlLibis[(S) -binaphthoxide] complex (ALB) to give the three-component coupling pro duct at room temperature in 92% ee and in 84% yield. The three-compone nt coupling product was then converted to (+)-11-deoxy-PGF(1 alpha) th rough several steps, including an oxidative decarboxylation, an aldol reaction, and a Wharton reaction. Moreover, the racemic enone, 20 was transformed into 21, the three-component coupling product, a potential intermediate for PGF(1 alpha), in 97% ee and in 75% yield through cat alytic kinetic resolution.