A new convenient synthesis of phenanthrene alkaloids from 1-arylmethyl-1,2,3,4-tetrahydroisoquinolines

Hofmann degradation of 1-arylmethyl-1,2,3,4-tetrahydro-2,2-dimethylisowuinolinium iodides with methanolic KOH gave stilbene derivatives, for example. (E)-N-2{2-[2-(phenyl)ethenyl]-4,5-dimethoxyphenyl}ethyl-N,N-dimethylamine. Photochemical electrocyclization of these stilbenes afforded the correspond...

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Bibliographic Details
Published inTetrahedron letters Vol. 45; no. 21; pp. 4171 - 4173
Main Authors Kini, SV, Ramana, MMV
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 17.05.2004
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
phenanthrenes
Hofmann elimination
stilbenes
phenanthrene alkaloids
photochemical electrocyclization
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Summary:Hofmann degradation of 1-arylmethyl-1,2,3,4-tetrahydro-2,2-dimethylisowuinolinium iodides with methanolic KOH gave stilbene derivatives, for example. (E)-N-2{2-[2-(phenyl)ethenyl]-4,5-dimethoxyphenyl}ethyl-N,N-dimethylamine. Photochemical electrocyclization of these stilbenes afforded the corresponding phenanthrene alkaloids/phenanthrene derivatives. (C) 2004 Published by Elsevier Ltd.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2004.03.127