Lumi-mestranol and epi-lumi-mestranol.
Treatment of lumi-estrone 3-methyl ether (I) with acetylene gave the C-17-epimeric compounds lumi-mestranol (3-methoxy-17 alpha-ethynyl-13 alpha-estra-1,3,5(10)-trien-17 beta-ol, III ) and epi-lumi-mestranol (3-methoxy-17 beta-ethynyl-13 alpha-estra-1,3,5(10)-trien-17 alpha-ol, IV). The structures of the two isomers were assigned on the basis of their molecular rotations and shift-reagent experiments in the NMR. The irradiation of estrone 3-methyl ether (II) to provide compound I was investigated in two solvent systems. Minor products of these reactions were the seco-steroids VII, VIII and X.
D000114:Acetylene; D055598:Chemical Phenomena; D002621:Chemistry; D004970:Estrone / Q000031:analogs & derivatives* / Q000528:radiation effects; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D008656:Mestranol / Q000138:chemical synthesis*; D012632:Secosteroids / Q000138:chemical synthesis; D013237:Stereoisomerism
D012632:Secosteroids; D004970:Estrone; C019372:estrone 3-methyl ether; D008656:Mestranol; D000114:Acetylene