title: A general efficient strategy for cis-3a-aryloctahydroindole alkaloids via stereocontrolled ZnBr(2)-catalyzed rearrangement of 2,3-aziridino alcohols.
abstract: A short and general approach to the cis-3a-aryloctahydroindole alkaloids has been developed on the basis of a key stereocontrolled ZnBr(2)-catalyzed rearrangement of 2,3-aziridino alcohols. Two representative members, (+/-)-crinane and (+/-)-mesembrine, have been synthesized in 15% and 11% overall yields, respectively. [reaction: see text]
authors.affiliation: Department of Chemistry and State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.
authors.forename: Zhen Lei
authors.initials: ZL
authors.lastname: Song
authors.forename: Bao Min
authors.initials: BM
authors.lastname: Wang
authors.forename: Yong Qiang
authors.initials: YQ
authors.lastname: Tu
authors.forename: Chun An
authors.initials: CA
authors.lastname: Fan
authors.forename: Shu Yu
authors.initials: SY
authors.lastname: Zhang
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D017967:Zinc Compounds / Q000737:chemistry*
chemical_list: D000438:Alcohols; D001388:Aziridines; D026121:Indole Alkaloids; D017967:Zinc Compounds