• 대한약학회:학술대회논문집
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• 대한약학회 2002년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2
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• pp.348.3-349
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• 2002

(－)-${\alpha}$-narcotine( 1 R.9S) is one of the major bases in Papaver somniferum L.. the sourse plant for opium. while (－)-${\beta}$-narcotine(1R.9R) is a synthetic phthalideisoquinoline alkaloid. Although some advanced methods for the preparation of $\alpha$-narcotine have been developed using modified Bischler-Napieralski cyclization. the facile synthesis of $\beta$-narcotine has not further been attempted. supposingly because of its no clinical efficacy contrary to $\alpha$-narcotine having an antitussive effect. (omitted)

• Bulletin of the Korean Chemical Society
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• 제34권4호
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• pp.1290-1292
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• 2013

• Bulletin of the Korean Chemical Society
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• 제23권11호
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• pp.1548-1552
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• 2002

$(-)-\beta-Narcotine$ (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 $iodo-{\beta}-narcotine$ (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.