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.
点击下载:
PDF (437KB)
返 回