Bulletin of the Korean Chemical Society

  • 제23권11호
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  • Pages.1548-1552
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  • 2002
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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(-)-β-Narcotine: A Facile Synthesis and the Degradation with Ethyl Choroformate

  • 발행 : 2002.11.20
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초록

$(-)-\beta-Narcotine$ (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.

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참고문헌

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피인용 문헌

  1. β-Phenylethylamines and the isoquinoline alkaloids vol.21, pp.3, 2004, https://doi.org/10.1039/B212259F
  2. Metal-Free Activation of a C(sp)−H Bond of Aryl Acetylenes vol.22, pp.42, 2016, https://doi.org/10.1002/chem.201603003
  3. )-H Bond, and a Practical and Rapid Synthesis of Privileged 1-Substituted 1,2,3,4-Tetrahydroisoquinolines vol.2017, pp.35, 2017, https://doi.org/10.1002/ejoc.201700471
  4. (-)-β-Narcotine: A Facile Synthesis and the Degradation with Ethyl Chloroformate. vol.34, pp.17, 2002, https://doi.org/10.1002/chin.200317188
  5. Stereochemistry of the Degradation Product of (-)-α-Narcotine and Its Analogs with Ethyl Chloroformate vol.15, pp.1, 2005, https://doi.org/10.5352/jls.2005.15.1.147
  6. Synthesis of microtubule-interfering halogenated noscapine analogs that perturb mitosis in cancer cells followed by cell death vol.72, pp.4, 2002, https://doi.org/10.1016/j.bcp.2006.05.004
  7. A New Total Synthesis of (±)-α-Noscapine vol.87, pp.12, 2013, https://doi.org/10.3987/com-13-12843