Add time:08/09/2019         Source:sciencedirect.com

9α-Hydroxyandrost-4-ene-3, 17-dione 1, when allowed to react with dipotassium acetylide in tetrahydrofuran, resulted, after chromatographic separation, in 4-methyl-19-norandrosta-4, 9-diene-1, 17-dione 2, 4ξ-methyl-19-norandrosta-5(10), 9(11)-diene-1, 17-dione 3. 4-methyl-17α-ethynyl-17β-hydroxy-19-norandrosta-4, 9-dien-1-one 4, 4ξ-methyl-17α-ethynyl-17ξ-hydroxy-19-norandrosta-5(10), 9(11)-dien-1-one 5, and 17α-ethynyl-17β-hydroxy-9, 10-secoandrost-4-ene-3, 9-dione 6. Selective protection of Δ4-3-ketone of 9α-hydroxyandrost-4-ene-3, 17-dione 1 as its dienol methyl ether 7, and subsequent reaction with lithium acetylide-ethylenediamine followed by acidic hydrolysis, afforded 9α, 17β-dihydroxy-17α-ethynylandrost-4-en-3-one 8.

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