Novel synthesis of 2-fluoroestradiol from 19-nortestosterone: biomimetic oxidative defluorination to 2-hydroxyestradiol.
A new, short synthetic route to 2-fluoroestradiol from 19-nortestosterone is described which gives the target compound in an approximately 25% overall yield. Oxidative defluorination of 2-fluoroestradiol to 2-hydroxyestradiol via treatment with Frémy's salt/iodide ion is reported. This process is regarded as biomimetic with respect to cytochrome P-450-dependent oxidative defluorination.
Le Quesne
P W
PW
Department of Chemistry, Northeastern University, Boston, MA 02115.
Allam
K
K
Abdel-Baky
S
S
Onan
K D
KD
Purdy
R H
RH
D055598:Chemical Phenomena; D002621:Chemistry; D004958:Estradiol / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D004967:Estrogens / Q000138:chemical synthesis*; D002393:Estrogens, Catechol; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009277:Nandrolone
D004967:Estrogens; D002393:Estrogens, Catechol; C037475:2-fluoroestradiol; D004958:Estradiol; D009277:Nandrolone; C001390:2-hydroxyestradiol