title: The chemistry of 9 alpha-hydroxy steroids. 2. Epimerization and functionalization of 17 alpha-ethynylated 9 alpha-hydroxy steroids.
abstract: Practical routes to 9 alpha-hydroxypregnenes were developed by epimerization and hydration of 17 alpha-ethynyl-9 alpha,17 beta-dihydroxyandrost-4-en-3-one. In the three different methods of epimerization which were used, the C-9 alpha hydroxy group was not susceptible to rearrangement or other side reactions. C-21 functionalized 9 alpha-hydroxypregnenes were obtained by introducing a 17 alpha-halogenated ethynyl group into 9 alpha-hydroxyandrost-4-ene-3,17-dione. Epimerization and hydration by the 17 beta-nitrooxy method produced 21-halogenated 9 alpha-hydroxypregnenes, which were further converted into 21-acetoxy-9 alpha-hydroxypregn-4-ene-3,20-dione.
authors.affiliation: Research & Development, Gist-brocades, Delft, The Netherlands.
authors.forename: J N
authors.initials: JN
authors.lastname: Batist
authors.forename: A F
authors.initials: AF
authors.lastname: Slobbe
authors.forename: A F
authors.initials: AF
authors.lastname: Marx
mesh_terms: D055598:Chemical Phenomena; D002621:Chemistry; D006914:Hydroxysteroids / Q000138:chemical synthesis*; D006915:Hydroxytestosterones; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
chemical_list: D006914:Hydroxysteroids; D006915:Hydroxytestosterones; C061919:17-ethynyl-9,17-dihydroxyandrost-4-en-3-one