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Model Studies Towards Stephaoxocanes: Construction of the 2‐Oxa‐4‐aza‐ phenalene Core of Stephaoxocanidine and Eletefine
Author(s) -
Bianchi Darío A.,
Cipulli Marcos A.,
Kaufman Teodoro S.
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300548
Subject(s) - isoquinoline , chemistry , ring (chemistry) , stereochemistry , core (optical fiber) , organic chemistry , materials science , composite material
The construction of the polysubstituted 1 H ,3 H ‐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