<unk> , also known as 3β-hydroxy-17α-ethynyl-19-nortestosterone 3β,17β-diaceate, 3β-hydroxynorethisterone 3β,17β-diacetate, or 17α-ethynylestr-4-ene-3β,17β-diol 3β,17β-diacetate, is a synthetic estrane steroid and a derivative of testosterone. It is specifically a derivative of 19-nortestosterone and 17α-ethynyltestosterone, or of norethisterone (17α-ethynyl-19-nortestosterone), in which the C3 ketone group has been dehydrogenated into a C3β hydroxyl group and acetate esters have been attached at the C3β and C17β positions.<unk>  is the 3β,17β-diacetate ester of<unk>  (17α-ethynylestr-4-ene-3β,17β-diol). Synthesis Searle). Prepn of the 3-acetate, 17-acetate, and<unk> : P. D. Klimstra, (1965 to Searle); see also: Chemical syntheses of<unk>  have been published. Reduction of norethisterone (1) affords the 3,17-diol. The 3β-hydroxy compound is the desired product; since reactions at C3 do not show nearly the stereoselectivity as those at C17 by virtue of the relative lack of stereo-directing proximate substituents, the formation of the desired isomer is engendered by use of a bulky reducing agent, lithium tri-tert-butoxyaluminum hydride. Acetylation of the 3β,17β-diol affords<unk>  (3).
Etynodiol diacetate
Bolandiol dipropionate
Tetramethyl bisphenol F
Chlormerodrin
Oxabolone cipionate
Beta-Zearalenol
Tienilic acid
Diethylstilbestrol disulfate