The reduction of 3-methoxy-estra-1,3,5(10)-trien-17β-ol (6) and 13-ethyl-3-ethoxy-gona-1,3,5(10)-triene-11α,17β-diol (2) by lithium in ethyl amine in the absence of a proton source is described. Both reductions, contrary to the reports of previous investigators, which indicated the 4-ene to be the main reaction product, gave a complex mixture of products. In the case of the reduction of 2, which is an intermediate in the synthesis of the progestagen desogestrel (1), we obtained the expected known 13-ethyl-gona-4-ene-11α,17β-diol (4) in small amounts and three new steroidal monoenes, 13-ethyl-gona-5(10)-ene-11α,17β-diol (11), 13-ethyl-gona-5(6)-ene-11α,17β-diol (12), and 13-ethyl-gona-1(10)-ene-11α,17β-diol (13). These compounds were characterized as the 11,17-diacetates with the 5(10)-ene 11 being the major compound.
Reduction of aromatic steroidal A rings by lithium in ethyl amine / E. Modica, D. Colombo, F. Compostella, A. Scala, F. Ronchetti. - In: STEROIDS. - ISSN 0039-128X. - 67:2(2002), pp. 145-150.
|Titolo:||Reduction of aromatic steroidal A rings by lithium in ethyl amine|
COLOMBO, DIEGO RODOLFO (Secondo)
SCALA, ANTONIO (Penultimo)
RONCHETTI, FIAMMA CLELIA VIRGINIA (Ultimo)
|Parole Chiave:||Desogestrel; Monoenes; Reduction; Steroids|
|Settore Scientifico Disciplinare:||Settore BIO/10 - Biochimica|
|Data di pubblicazione:||2002|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1016/S0039-128X(01)00145-3|
|Appare nelle tipologie:||01 - Articolo su periodico|