title: Heterocyclic steroids: synthesis of steroidal selena, tellura, and thialactones of estrane series.
abstract: A successful approach in the synthesis of 3 beta-acetoxy-17a-selena-D-homo-1,3,5(10)-estratrien-17 -one (5), 3 beta-acetoxy-17a tellura-D-homo-1,3,5(10)-estratrien-17-one (6), and 3 beta-acetoxy-17a-thia-D-homo-1,3,5(10)-estratrien-17-one (7) was achieved from 3 beta-acetoxy-1,3,5(10)-estratrien-17-one (1). The Baeyer-Villiger reaction of 3 beta-acetoxy-1,3,5(10)-estratrien-17-one (1) with perbenzoic acid afforded 3 beta-acetoxy-17a-oxa-D-homo-1,3,5(10)-estratrien-17-one (2), which on reaction with hydrobromic acid gave 3 beta-acetoxy-seco-13-bromo-1,3,5(10)-estratrien-16-oic acid (3). Treatment of bromo acid (3) with thionyl chloride gave 3 beta-acetoxy-seco-13-bromo-1,3,5(10)-estratrien-17 acid chloride (4), whose reaction with Se and Te in the presence of sodium borohydride gave the desired products 5 and 6. Reaction of 3 beta-acetoxy-seco-13-bromo-1,3,5(10)-estratrien-17 acid chloride (4) with sodium sulfide gave the thia lactone derivative (7).
authors: Department of Chemistry, Nizam College, Osmania University, Hyderabad, India.
authors: A U
authors: AU
authors: Siddiqui
authors: Y
authors: Y
authors: Satyanarayana
authors: I
authors: I
authors: Ahmed
authors: A H
authors: AH
authors: Siddiqui
mesh_terms: D015394:Molecular Structure; D013256:Steroids / Q000138:chemical synthesis*
chemical_list: D013256:Steroids