A facile asymmetric route to (-)-aphanorphine

被引：45
|
作者：
Zhai, HB
Luo, SJ
Ye, CF
Ma, YX
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Lab Modern Synth Organ Chem, Shanghai 200032, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
[3] Lanzhou Univ, Dept Chem, Lanzhou 730000, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 21期
关键词：
D O I：
10.1021/jo0348726
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
80-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.
引用
收藏
页码：8268 / 8271
页数：4
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