LAUSR

Graphical abstract Figure. No caption available. HighlightsStereoselective synthesis of diastereomeric diols.Straightforward synthetic route from trans‐ to cis‐diols.Substantial antiproliferative action against HeLa. &NA; The reduction of 16‐hydroxymethylene‐3‐methoxy‐13&agr;‐estra‐1,3,5(10)‐trien‐17‐one (14) and 16‐hydroxymethylene‐3‐benzyloxy‐13&agr;‐estra‐1,3,5(10)‐trien‐17‐one (16) yielded a mixture of two diastereomeric diols, the 16&agr;‐hydroxymethyl,17&bgr;‐hydroxy and 16&bgr;‐hydroxymethyl,17&agr;‐hydroxy isomers (17a‐20a) in a ratio of 6:1. We describe a straightforward synthetic route to transform the isomers with trans functional groups attached to ring D (17a‐20a) into isomers with cis functional groups (25a‐28a). We determined the in vitro antiproliferative activities of compounds 17a–20a and 25a–28a by means of MTT assays against a panel of human adherent cancer cell lines HeLa, A2780, MCF‐7, T47D, MDA‐MB‐231 and MDA‐MB‐361.