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Novel Stereoselective Synthesis and Chromatographic Evaluation of E-guggulsterone

Antimo Gioiello, Roccaldo Sardella, Emiliano Rosatelli, Bahman M Sadeghpour, Benedetto Natalini, Roberto Pellicciari

Steroids. 2012 Feb;77(3):250-4.

PMID: 22155267

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP39025246 (E)-Guggulsterone (E)-Guggulsterone 39025-24-6 Price
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