(-)-¥â-Narcotine: A Facile Synthesis and the Degradation with Ethyl Chloroformate

Bulletin of the Korean chemical society

Dong-Ung Lee¹ 

关键词: (-)- b-Narcotine;    Facile synthesis;    Ring cleavage;    Ethyl chloroformate;   

DOI  :  

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

(-)-β-Narcotine (6), a phthalideisoquinoline alkaloid, was synthesized conveniently by the direct condensation of cotarnine (1) and iodomeconine (2) prepared by aromatic iodination using thallium trifluoroacetate/KI and by the successive reduction of resulting iodo-β-narcotine (5) with aluminum amalgam. Its structure including a stereochemistry was confirmed by instrumental analyses. This synthetic alkaloid was degraded with ethyl chloroformate at room temperature to afford the chloro-carbamate 6b as a crystalline intermediate, which was unexpectedly converted into the carbinol 8 by exchange of Cl with OH of water contained in the solvents and the ethoxy-carbamate 9, probably because of ethanol added to chloroform as a solvent stabilizer during the purification by column chromatography.

【 授权许可】

Unknown