Über die photochemische cis-trans-Isomerisierung des Annulolins

6533b82bfe1ef96bd128e01b

RESEARCH PRODUCT

Über die photochemische cis-trans-Isomerisierung des Annulolins

subject

Chemistry Stereochemistry Drug Discovery Pharmaceutical Science

description

Das Alkaloid Annulolin wird in den Wurzeln von Lolium multiflorum Lam. als trans-2-(3,4-Dimethoxystyryl)-5-(4-methoxyphenyl)-oxazol gebildet. Unter Lichteinflus unterliegt es einer cis-trans-Isomerisierung. Es gelang, die Isomere zu trennen. Wahrend im trans-Annulolin eine planare Einebnung des Molekuls moglich ist, wurden sich bei Einebnung des cis-Isomers die Wirkungsspharen von Stickstoff und orthostandigem Wasserstoff uberschneiden. cis-Annulolin ist infolge dieser Hinderung und der dadurch verursachten Storung des Resonanzsystems fluoreszenzunfahig. Fur die photochemische cis-trans-Isomerisierung ist ein Konjugationssystem wie das des Stilbens oder 2-Styryloxazols erforderlich. Die Erscheinung der Umlagerung wird diskutiert.

year	journal	country	edition	language
1965-01-01	Archiv der Pharmazie

https://doi.org/10.1002/ardp.19652980904

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