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.

Reduction of aromatic steroidal A rings by lithium in ethyl amine

D. Colombo
Secondo
;
F. Compostella;A. Scala
Penultimo
;
F. Ronchetti
Ultimo
2002

Abstract

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.
Desogestrel; Monoenes; Reduction; Steroids
Settore BIO/10 - Biochimica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/182022
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