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Conversion of Hydrastine into Berberine, and an Instance of the Asymmetrical Quaternization of a Tertiary Base

Abstract

THE molecule of narcotine contains two asymmetric carbon atoms, IQ in the isoquinoline nucleus and P in the phthalide nucleus. The action of strong bases under suitable conditions racemizes P but leaves IQ unchanged1. Thus natural 1-α-narcotine is partly transformed into 1-β-narcotine; − IQ, − P IQ, + P.

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References

  1. Marshall, Pyman and Robinson, J. Chem. Soc., 1315 (1934).

  2. Perkin, J. Chem. Soc., 118, 737 (1918).

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  3. Perkin and Robinson, J. Chem. Soc., 97, 305 (1910).

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MIRZA, R., ROBINSON, R. Conversion of Hydrastine into Berberine, and an Instance of the Asymmetrical Quaternization of a Tertiary Base. Nature 166, 271–272 (1950). https://doi.org/10.1038/166271a0

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