title: Novel stereoselective synthesis and chromatographic evaluation of E-guggulsterone.
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.
authors.affiliation: Dipartimento di Chimica e Tecnologia del Farmaco, Università di Perugia, Via del Liceo 1, 06123 Perugia, Italy.
authors.forename: Antimo
authors.initials: A
authors.lastname: Gioiello
authors.forename: Roccaldo
authors.initials: R
authors.lastname: Sardella
authors.forename: Emiliano
authors.initials: E
authors.lastname: Rosatelli
authors.forename: Bahman M
authors.initials: BM
authors.lastname: Sadeghpour
authors.forename: Benedetto
authors.initials: B
authors.lastname: Natalini
authors.forename: Roberto
authors.initials: R
authors.lastname: Pellicciari
mesh_terms: D000736:Androstenes / Q000737:chemistry; D002219:Carbamates / Q000737:chemistry; D002482:Cellulose / Q000031:analogs & derivatives / Q000737:chemistry; D002725:Chloroform / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000379:methods* / Q000592:standards; D029744:Commiphora / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011282:Pregnenediones / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry*; D015203:Reproducibility of Results; D058428:Silica Gel / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000736:Androstenes; D002219:Carbamates; D011282:Pregnenediones; C509199:cellulose 3,5-dimethylphenylcarbamate; D058428:Silica Gel; D002725:Chloroform; D002482:Cellulose; C023617:pregna-4,17-diene-3,16-dione