Degradation of 1-Benzyl-1,2,3,4-tetrahydroisoquinolines (Laudanosine) with Ethyl chloroformate: Gedamer's Intermediate

URN to cite this document:: urn:nbn:de:bvb:355-epub-156947
DOI to cite this document:: 10.5283/epub.15694

Angerer, S. von ; Eibler, E. ; Lee, D.-U. ; Wiegrebe, Wolfgang

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Date of publication of this fulltext: 08 Jul 2010 04:45

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Item type:	Article
Journal or Publication Title:	Scientia Pharmaceutica (Sci. Pharm.)
Volume:	57
Page Range:	pp. 1-6
Date:	1989
Institutions:	Chemistry and Pharmacy > Institute of Pharmacy > Alumni or Retired Professors > Prof. Wiegrebe
Keywords:	1-Benzyl-1,2,3,4-tetrahydroisoquinolines, Ethyl chloroformate, Mosher-Esters
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:	15694

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Abstract

Gadamer has postulated the α-chlorobisbenzyl derivate 2a as an intermediate of the degradation of laudanosine [(-)-1] to the stilbene 3 by ethyl chloroformate. Optically active 2a is easily hydrolyzed to the corresponding carbinol 2b. The optical purity of 2b is determined via diastereomeric esters. Als Zwischenprodukt des Chlorameisensäureethylester-Abbaus von Laudanosin [(-)-)1] zum Stilben 3 ...

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