A versatile synthesis of 17-heteroaryl androstenes via palladium-mediated Suzuki cross-coupling with heteroaryl boronic acids

Suzuki coupling of 17-iodoandrosta-5,16-dien-3β-ol (1) and 17-iodoandrosta-4,16-dien-3-one (2) with nine heteroaryl boronic acids (mainly 2- or 3-furanyl, thienyl, benzofuranyl and benzothienyl boronic acid derivatives) were carried out under normal Suzuki condition (Pd(PPh3)4, 2 M Na2CO3 and MeOH), generally yielded C17-heteroaryl steroids in moderate (10–60%) yields, but furanyl-2- and 5-chlorothienyl-2-boronic acid did not give any coupling product.