Degradation of some Phthalideisoquinolines with Ethyl Chloroformate-Stereochemical Aspects

URN to cite this document:: urn:nbn:de:bvb:355-epub-157286
DOI to cite this document:: 10.5283/epub.15728

Lee, D.-U. ; Iwasa, K. ; Kamigauchi, M. ; Takao, N. ; Wiegrebe, Wolfgang

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Date of publication of this fulltext: 08 Jul 2010 05:08

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Item type:	Article
Journal or Publication Title:	Chemical & Pharmaceutical Bulletin
Volume:	39
Number of Issue or Book Chapter:	8
Page Range:	pp. 1944-1948
Date:	1991
Institutions:	Chemistry and Pharmacy > Institute of Pharmacy > Alumni or Retired Professors > Prof. Wiegrebe
Keywords:	α-narcotine; β-narcotine; α-hydrastine; β-hydrastine; ethyl chloroformate; diastereoselectivity; enantiomer; diastereomeric carbinol; enol lactone; X-ray analysis; absolute configuration
Dewey Decimal Classification:	500 Science > 540 Chemistry & allied sciences
Status:	Published
Refereed:	Yes, this version has been refereed
Created at the University of Regensburg:	Unknown
Item ID:	15728

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Abstract

Treatment of phthalideisoquinolines such as α- (1) and β-narcotine (2) as well as ß-(3) and α-hydrastine (4) with ethyl chloroformate (ECF) at room temperature afforded, via the chloro-carbamates, the corresponding diastereomeric carbinols with high stereoselectivity. Instrumental analyses of each diastereomeric pair indicate that the major isomers derived from α- and β-narcotine as well as from ...

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