title: Synthesis of A B C-ring subunit of C-nor-D-homo-steroidal alkaloids: towards the total synthesis of cyclopamine.
abstract: A practical approach to the synthesis of the A, B and C-ring subunit of cyclopamine has been developed. This synthetic tactic highlights the utility of mandelate acetal-mediated resolution of the fused ring ketone (±)-4 and IBX-mediated oxidation cascades from 12 to 9. The availability of advanced intermediates from enantiomerically pure (+)-4 and 2 could provide efficient access to biologically active and structurally diverse C-nor-D-homo-steroidal alkaloids such as cyclopamine.
authors.affiliation: Center for Drug Discovery, College of Pharmacy, China Pharmaceutical University, Nanjing, China.
authors.forename: Xue-Li
authors.initials: XL
authors.lastname: Zhang
authors.forename: Yu-Qi
authors.initials: YQ
authors.lastname: Liao
authors.forename: Peng-Jun
authors.initials: PJ
authors.lastname: Cai
authors.forename: He-Quan
authors.initials: HQ
authors.lastname: Yao
authors.forename: Ling-Yi
authors.initials: LY
authors.lastname: Kong
authors.forename: Hong-Bin
authors.initials: HB
authors.lastname: Sun
mesh_terms: D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D015394:Molecular Structure; D055601:Organic Chemistry Phenomena; D013237:Stereoisomerism; D013256:Steroids / Q000737:chemistry; D014704:Veratrum Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D013256:Steroids; D014704:Veratrum Alkaloids; C000541:cyclopamine