title: A facile asymmetric route to (-)-aphanorphine.
abstract: 8O-methylaphanorphine was synthesized from 4-methoxyphenylacetaldehyde in 36% overall yield and in nine steps, featuring the formation of ring B via a Friedel-Crafts alkylative cyclization with the concomitant stereospecific introduction of the benzylic quaternary carbon center. The current work constitutes an efficient enantioselective formal synthesis of 3-benzazepine marine alkaloid (-)-aphanorphine.
authors.affiliation: Laboratory of Modern Synthetic Organic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China. zhaih@mail.sioc.ac.cn
authors.forename: Hongbin
authors.initials: H
authors.lastname: Zhai
authors.forename: Shengjun
authors.initials: S
authors.lastname: Luo
authors.forename: Chengfeng
authors.initials: C
authors.lastname: Ye
authors.forename: Yongxiang
authors.initials: Y
authors.lastname: Ma
mesh_terms: D000079:Acetaldehyde / Q000031:analogs & derivatives* / Q000737:chemistry*; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001952:Bridged-Ring Compounds; D011758:Pyrroles; C434304:aphanorphine; D000079:Acetaldehyde; C013192:phenylacetaldehyde