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.
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.
Curts
S W
SW
Institute of Organic Chemistry, Syntex Research, Palo Alto, CA 94304.
Wren
D L
DL
Cooper
G F
GF
D006801:Humans; D015394:Molecular Structure; D009640:Norethindrone / Q000378:metabolism*; D009641:Norethynodrel / Q000031:analogs & derivatives* / Q000138:chemical synthesis
C003578:17-ethynyl-5-estrane-3,17-diol; D009641:Norethynodrel; D009640:Norethindrone