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 con...

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Bibliographic Details
Published in:Journal of organic chemistry 2003-10, Vol.68 (21), p.8268-8271
Main Authors: Zhai, Hongbin, Luo, Shengjun, Ye, Chengfeng, Ma, Yongxiang
Format: Article
Language:English
Subjects:
Acetaldehyde - analogs & derivatives
Acetaldehyde - chemistry
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Bridged-Ring Compounds - chemical synthesis
Bridged-Ring Compounds - chemistry
Chemistry
Exact sciences and technology
Molecular Structure
Organic chemistry
Preparations and properties
Pyrroles - chemical synthesis
Pyrroles - chemistry
Stereoisomerism
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0348726