Model Studies Towards Stephaoxocanes: Construction of the 2-Oxa-4-aza- phenalene Core of Stephaoxocanidine and Eletefine

The construction of the polysubstituted 1H,3H‐2‐oxa‐4‐azaphenalene 4 by means of consecutive oxa‐Pictet−Spengler and Jackson cyclizations is reported. This compound contains the ABC ring system of the novel isoquinoline alkaloids stephaoxocanidine and eletefine, found in Stephania cepharantha and Ci...

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Published inEuropean journal of organic chemistry Vol. 2003; no. 24; pp. 4731 - 4736
Main Authors Bianchi, Darío A., Cipulli, Marcos A., Kaufman, Teodoro S.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 01.12.2003
WILEY‐VCH Verlag
Wiley
Subjects
Chemistry
Chemistry, Organic
Cyclization
Electrophilic substitution
Natural products
Nitrogen heterocycles
Physical Sciences
Science & Technology
natural products
STEREOSELECTIVE ISOMERIZATIONS
ENANTIOSELECTIVE SYNTHESIS
ADRENERGIC-RECEPTOR ANTAGONIST
nitrogen heterocycles
STEPHANIA
CHLORIDES
ROOTS
RING-SYSTEM
cyclization
DERIVATIVES
electrophilic substitution
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Summary:The construction of the polysubstituted 1H,3H‐2‐oxa‐4‐azaphenalene 4 by means of consecutive oxa‐Pictet−Spengler and Jackson cyclizations is reported. This compound contains the ABC ring system of the novel isoquinoline alkaloids stephaoxocanidine and eletefine, found in Stephania cepharantha and Cissampelos glaberrima. Both these species are Menispermaceæ used in folk medicine in the Far East and Brazil. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003
Bibliography:ArticleID:EJOC200300548
istex:EBEAA97E477FB0C227A5D82B69C318A953AC84C5
ark:/67375/WNG-4CSJ2ZBZ-G
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200300548