title: Synthesis of 5 beta,17 alpha-19-norpregn-20-yne-3 beta,17-diol and of 5 beta,17 alpha-19-norpregn-20-yne-3 alpha,17-diol, human metabolites of norethindrone.
abstract: A convenient synthesis of both 5 beta,17 alpha-19-norpregn-20-yne-3 beta,17-diol (1) and 5 beta,17 alpha-19-norpregn-20-yne-3 alpha,17-diol (2) in multigram quantities from estr-4-ene-3,17-dione is reported. Full characterization of these often-cited human metabolites of norethindrone is presented for the first time.
authors.affiliation: Institute of Organic Chemistry, Syntex Research, Palo Alto, CA 94304.
authors.forename: S W
authors.initials: SW
authors.lastname: Curts
authors.forename: D L
authors.initials: DL
authors.lastname: Wren
authors.forename: G F
authors.initials: GF
authors.lastname: Cooper
mesh_terms: D006801:Humans; D015394:Molecular Structure; D009640:Norethindrone / Q000378:metabolism*; D009641:Norethynodrel / Q000031:analogs & derivatives* / Q000138:chemical synthesis
chemical_list: C003578:17-ethynyl-5-estrane-3,17-diol; D009641:Norethynodrel; D009640:Norethindrone