Synthesis of 3-carboxy-20-keto steroid, SB 209963, a 5α-reductase inhibitor, by palladium-catalyzed hydroxycarbonylation

Article abstract of DOI:10.1016/S0040-4039(99)00456-6

SB 209963 was produced in three steps starting from 17β- carboxyandrost-4-en-3-one. A palladium-catalyzed hydroxycarbonylation introduced the carboxylic acid under mild conditions withOUt epimerization at C17. This reaction represents the first example of hydroxycarbonylation of a vinyl halide under neutral conditions.