Synthetic studies towards steroid-amino acid hybrids

Abstract

New prototype of natural steroid amino acid hybrid containing nine membered D-ring in the steroid skeleton has been synthesized from commercially available estrone using standard synthetic organic transformations. NaIO4 cleavage of the D-ring of the benzylated estriol furnishes the D-seco diol 8, which after a series of organic reactions (protection of the hydroxyl group, oxidation, reductive amination, deprotection and the Yamaguchi cross coupling) gives the coveted steroid-amino acid hybrids. The methodology can be extended for combinatorial synthesis of new and interesting steroid amino acid hybrids.