The chemistry of 9 alpha-hydroxysteroids. 1. Preparation of 9 alpha,17 beta-dihydroxy-17 alpha-ethynylandrost-4-en-3-one.
9 alpha-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, 4 xi-methyl-19-norandrosta-5(10),9(11)-diene-1,17-dione 3, 4-methyl-17 alpha-ethynyl-17 beta-hydroxy-19-norandrosta-4,9-dien-1-one 4, 4 xi-methyl-17 alpha-ethynyl-17 beta-hydroxy-19-norandrosta-5(10),9(11)-dien- 1-one 5, and 17 alpha-ethynyl-17 beta-hydroxy-9,10-secoandrost-4-ene-3,9-dione 6. Selective protection of delta 4-3-ketone of 9 alpha-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 9 alpha,17 beta-dihydroxy-17 alpha- ethynylandrost-4-en-3-one 8.
Kapur
J C
JC
Research & Development, Delft, The Netherlands.
Marx
A F
AF
Verweij
J
J
D000305:Adrenal Cortex Hormones / Q000138:chemical synthesis; D055598:Chemical Phenomena; D002621:Chemistry; D006914:Hydroxysteroids; D006915:Hydroxytestosterones / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013739:Testosterone / Q000031:analogs & derivatives*
D000305:Adrenal Cortex Hormones; D006914:Hydroxysteroids; D006915:Hydroxytestosterones; C060444:9,17-dihydroxy-17-ethynylandrost-4-en-3-one; D013739:Testosterone