Collect. Czech. Chem. Commun. 2002, 67, 47-54

Synthesis of cis and trans Isomers of D-Ring Linked Bis-Steroid Pyrazines from 16α-Bromo-17-oxosteroids

Zenon Łotowski*, Jacek W. Morzycki, Izabella S. Niewczas and Marta Zdanowicz

Institute of Chemistry, University of Bialystok, al. Pilsudskiego 11/4, 15-443 Bialystok, Poland


Treatment of 16α-bromo-17-oxosteroids 1 and 2 with gaseous ammonia and successive air-oxidation afforded the cis and trans isomers of D-linked bis-steroid pyrazines. Analogous reaction of 1α-bromo-4-nor-5α-cholestan-2-one (3) led to unexpected hydrolysis products.

Keywords: Steroids; Bis-steroidal pyrazines; α-Bromo ketones; Enamines; Cephalostatin analogs.

References: 18 live references.