A COMMON AND GENERAL ACCESS TO BERBERINE AND BENZO[C]PHENANTHRIDINE ALKALOIDS

The S(RN)1 reactions between o-iodobenzamides and the enolate anion from 2-acetyl homoveratric acid lead to key tricyclic compounds which are easily converted to either berberine or benzo [c] phenanthridine ring systems providing thus a high-yielding and versatile access to both classes of alkaloids...

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Bibliographic Details
Published inTetrahedron Vol. 48; no. 38; pp. 8285 - 8294
Main Authors BEUGELMANS, R, BOISCHOUSSY, M
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 1992
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
TRANSFORMATION
3-ARYL ISOQUINOLONES
BERBERINES
PROTOBERBERINES
SRN1
BENZOPHENANTHRIDINE ALKALOIDS
EFFICIENT SYNTHESIS
ACID METHYL-ESTER
FAGARONINE
BENZOPHENANTHRIDINES
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Summary:The S(RN)1 reactions between o-iodobenzamides and the enolate anion from 2-acetyl homoveratric acid lead to key tricyclic compounds which are easily converted to either berberine or benzo [c] phenanthridine ring systems providing thus a high-yielding and versatile access to both classes of alkaloids.
ISSN:0040-4020
DOI:10.1016/S0040-4020(01)80496-8