Stereoselective halogenation of the 16-hydroxymethyl-3-methoxy-13alpha-estra-1,3,5(10)-trien-17-ols and their solvolytic investigation.
The primary hydroxy functions of 16alpha-hydroxymethyl-3-methoxy-13alpha-estra-1,3,5(10)-trien-17beta-ol (3a) and 16beta-hydroxymethyl-3-methoxy-13alpha-estra-1,3,5(10)-trien-17alpha-ol (4a) were stereoselectively transformed into good leaving groups. On alkaline methanolysis of the 16-halomethyl or 16-tolylsulfonyloxymethyl derivatives, a new D-seco-13alpha-estrone derivative was obtained in high yield.
Wölfling
János
J
Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary.
Mernyák
Erzsébet
E
Forgó
Péter
P
Schneider
Gyula
G
D001966:Bromine / Q000737:chemistry; D002713:Chlorine / Q000737:chemistry; D004964:Estriol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D006219:Halogens / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis / Q000737:chemistry; D007455:Iodine / Q000737:chemistry; D008956:Models, Chemical; D012997:Solvents / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D006219:Halogens; D006846:Hydrocarbons, Halogenated; D012997:Solvents; C037863:estra-1,3,5(10)-triene-3,7,17-triol; D002713:Chlorine; D007455:Iodine; D004964:Estriol; D001966:Bromine