Thermodynamic Meerwein-Ponndorf-Verley reduction in the diastereoselective synthesis of 17α-estradiol.
Steroids
; 113: 1-4, 2016 09.
Article
in En
| MEDLINE
| ID: mdl-27137355
ABSTRACT
The synthesis of 17α-hydroxy steroids generally requires multiple synthetic manipulations. The synthesis of 17α-estradiol is no exception, as this process involves the protection and release of the 3-hydroxy functional group. The diastereoselective reduction of the 17-keto-steroid can be utilized to prepare 17α-hydroxy-steroids. Here, 17α-estradiol was synthesized from commercially available estrone under thermodynamic Meerwein-Ponndorf-Verley (MPV) conditions in a single step, followed by simple chromatographic separation over silica gel. The remaining mixture of unreacted estrone and estradiols was easily recycled through Oppenauer oxidation to estrone, with an overall yield of 68% 17α-estradiol.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Thermodynamics
/
Estradiol
Language:
En
Journal:
Steroids
Year:
2016
Document type:
Article