Synthesis of (17R)- and (17S)-17-hydroxy-14, 15-secoandrost-4-en-16-yn-3- one and the X-ray crystal structure of the (17S)-diastereomer

Article abstract of DOI:10.1016/0039-128X(94)00044-D

(17R, S)-17-Hydroxy-14,15-secoandrost-4-en-15-yn-3-one has been shown previously to be a mechanism-based inactivator of rat liver 3α- hydroxysteroid dehydrogenase. This manuscript describes the synthesis of this diastereomeric 14,15-secosteroid from [2S-2