Practical one-pot conversion of 17beta-estradiol to 10beta-hydroxy- (p-quinol) and 10beta-chloro-17beta-hydroxyestra-1,4-dien-3-one.
An efficient one-pot procedure for the preparation of 10beta,17beta-dihydroxyestra-1,4-dien-3-one (p-quinol, 1, 75%) is reported, involving oxidation of 17beta-estradiol with potassium permanganate. Similar treatment of 17beta-estradiol with sodium chlorite led to 10beta-chloro-17beta-hydroxyestra-1,4-dien-3-one (2) in 44% yield along with smaller amounts 4-chloro-10beta,17beta-dihydroxyestra-1,4-dien-3-one (3), 2,10beta-dichloro-17beta-hydroxyestra-1,4-dien-3-one (4), and 4,10beta-dichloro-17beta-hydroxyestra-1,4-dien-3-one (5).
Lista
Liliana
L
Department of Organic Chemistry and Biochemistry, University of Naples Federico II, Italy.
Manini
Paola
P
Napolitano
Alessandra
A
Pezzella
Alessandro
A
d'Ischia
Marco
M
D004958:Estradiol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*; D004963:Estrenes / Q000138:chemical synthesis; D006873:Hydroquinones / Q000138:chemical synthesis*; D008954:Models, Biological; D008968:Molecular Conformation
C514144:10beta-chloro-17beta-hydroxyestra-1,4-dien-3-one; D004963:Estrenes; D006873:Hydroquinones; D004958:Estradiol