Abstract
Steroids with a thiophene ring fused to the 2, 3 positions were synthesized. Condensation of 2-methoxymethylene-3-ketosteroids (Ia, Ib) with ethyl thioglycolate in the presence of sodium methoxide yielded the tetrahydrothiophene derivatives (Va, Vb), which were dehydrated to the corresponding androstano [2, 3-c] thiophene carboxylates (VIa, VIb) by treatment of acids. Hydrolysis, followed by decarboxylation of the carbethoxythiophenes gave the corresponding androstano [2, 3-c] thiophenes (Xa, Xb). Similarly androst-4-eno [2, 3-c] thiophenes and androstanc [16, 17-c] thiophenes were prepared.
