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A Chiral Synthesis of (+)-Pseudoconhydrine

 

作者: Kin-Ichi Tadano,   Youichi Iimura,   Tetsuo Suami,  

 

期刊: Journal of Carbohydrate Chemistry  (Taylor Available online 1985)
卷期: Volume 4, issue 2  

页码: 129-139

 

ISSN:0732-8303

 

年代: 1985

 

DOI:10.1080/07328308508058828

 

出版商: Taylor & Francis Group

 

数据来源: Taylor

 

摘要:

(+)-Pseudoconhydrine, one of hemlock alkaloids, has been synthesized from methyl 2-acetamido-2,3,4-trideoxy-α-D-erythro-hexopyranoside by an eleven step reaction sequence. An intramolecular nucleophilic attack of the nitrogen atom on 2-acetamido-5-0-benzyl-2,3,4-trideoxy-6-0-tosyl-D-reythro-hexose diethyl di-thioacetal to the terminal tosyloxymethylene group proceeded smoothly and gave the desired disubstituted piperidine compound. A conversion of the thioacetal group into an aldehyde, a two-carbon elongation by Wittig olefination, and a successive hydro-genation completed the chiral synthesis of the title alkaloid.

 

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