Open AccessTricyclic Marine Alkaloids: Synthetic Approaches to Cylindricines, Lepadiformine, and Fasicularin
Author(s) -
Pascal Schär,
Sylvaine Cren,
Philippe Renaud
Publication year - 2006
Publication title -
chimia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.387
H-Index - 55
eISSN - 2673-2424
pISSN - 0009-4293
DOI - 10.2533/000942906777674976
Subject(s) - natural product , quinoline , tricyclic , combinatorial chemistry , chemistry , stereochemistry , carbon skeleton , computational biology , biology , organic chemistry
Cylindricines, lepadiformine, and fasicularin are marine alkaloids with a common novel pyrrolo- and pyrido[1,2-j]quinoline skeleton. They have recently been isolated from various tunicates and have shown interesting cytotoxic effects which could be attributed to covalent interactions with DNA, as well as cardiovascular effects. The promising biological activities together with the unique structural features make these alkaloids interesting targets for natural product synthesis. This review focuses on the different approaches developed for their synthesis with a particular emphasis on the key step where the quaternary amino substituted carbon center is created.