1. Novel stereoselective synthesis and chromatographic evaluation of E-guggulsterone
- Author
-
Gioiello, Antimo, Sardella, Roccaldo, Rosatelli, Emiliano, Sadeghpour, Bahman M., Natalini, Benedetto, and Pellicciari, Roberto
- Subjects
- *
STEROIDS , *OXIDATION , *ANDROSTENEDIONE , *WITTIG reaction , *CELLULOSE , *CHLOROFORM , *HIGH performance liquid chromatography - Abstract
Abstract: A new stereoselective synthesis of E-guggulsterone is described starting from androsten-3,17-dione. Protection of the ring A enonic system, followed by regioselective Wittig reaction and C-16 oxidation, affords E-guggulsterone in good yields and high stereoselectivity, making this approach easily accessible and scalable. Moreover, an original normal-phase HPLC method enabling the fast quantitation of the guggulsterone isomeric purity, combined with the suitability for sampling procedures, is detailed. The relying upon the cellulose-based Chiralpak IB column and the chloroform as the “non-standard” component of the eluent mixture, allows to get profitably high chromatographic performances. [Copyright &y& Elsevier]
- Published
- 2012
- Full Text
- View/download PDF