The reaction between dehydroepiandrosterone (I) and acetylene in the presence of potassium /-amyl oxide, which is known to yield 17a-ethinyl-A5-androstene-3/3,17d-diol (Ila) as the major product, has been shown to produce di-17a-(A5-androstene-30,17/5-diol)-acetylene_(IVa) as a by-product. The dehydration, Oppenauer oxidation and complete hydrogenation of the tetrol IVa are described. The reaction between dehydroepiandrosterone (I) and acetylenedimagnesium bromide does not lead to the tetrole IVa, but produces 17a-ethinyl-Ae-androstene-3/3,17/3-diol (Ila) in excellent yield.
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