A facile asymmetric route to (-)-aphanorphine.
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.
Zhai
Hongbin
H
Laboratory of Modern Synthetic Organic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China. zhaih@mail.sioc.ac.cn
Luo
Shengjun
S
Ye
Chengfeng
C
Ma
Yongxiang
Y
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
D001952:Bridged-Ring Compounds; D011758:Pyrroles; C434304:aphanorphine; D000079:Acetaldehyde; C013192:phenylacetaldehyde