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Ring-cleavage of Phthalidisoquinoline Alkaloids by Ethyl Chloroformate

URN to cite this document:
urn:nbn:de:bvb:355-epub-157432
Angerer, S. von ; Angerer, E. von ; Ambros, R. ; Wiegrebe, Wolfgang
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Date of publication of this fulltext: 12 Jul 2010 07:35


Abstract

Degradation of (-)-α-narcotine (5), (-)-ß-narcotine (6), and (-)-ß-hydrastine (7) with ethyl chloroformate (ECF) affords the chloro-urethans 9 and 18, respectively. Diastereomer 9-1 is easily hydrolyzed to the hydroxy-urethan 10, whilst 18 is converted to the methoxy-analogue 19. The stilbene lactone 11 is obtained from 9-1 by treatment with DBU, the analogous stilbene 17 arises already when 7 is ...

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