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KMID : 0613820050150010147
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Journal of Life Science
2005 Volume.15 No. 1 p.147 ~ p.151
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Stereochemistry of the Degradation Product of (-)-α-Narcotine and Its Analogs with Ethyl Chloroformate
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Lee Dong-Woong
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Abstract
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A (-)-α-narcotine from Papaver sommiferum was refluxed with ethyl chloroformate to give the diastereomeric chloro-carbamate mixture and the Z/E-enol lactones as Z:E=1:1.1 ratio in HPLC analysis. After photoisomerization with UV (254 ㎚), the Z/E ratio was drastically changed to Z:E=7:1, which may indicate that the E-isomer was easily converted to the Z-isomer due to photoisomerization. The photoisomerization of the Z/E-enol lactones and the different stereochemistry of the degradation product of β-narcotine, deuterated β-narcotine and β-hydrastine with ethyl chloroformate will also be discussed.
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KEYWORD
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