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Pachychalines A–C: Novel 3‐Alkylpyridinium Salts from the Marine Sponge Pachychalina sp.
Author(s) -
Laville Rémi,
Thomas Olivier P.,
Berrue Fabrice,
Reyes Fernando,
Amade Philippe
Publication year - 2008
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.200700741
Subject(s) - pyridinium , chemistry , sponge , nuclear magnetic resonance spectroscopy , stereochemistry , pyridinium compounds , organic chemistry , botany , biology
Three 3‐alkylpyridinium salts, pachychalines A ( 1 ), B ( 2 ) and C ( 3 ), were isolated from the Caribbean marine sponge Pachychalina sp. (order Haplosclerida). They are the first examples of 3‐(aminoalkyl)pyridinium salts. Their chemical structures were elucidated by NMR spectroscopy and detailed ESI HRMS–MS analysis. The total synthesis of 1 allowed the confirmation of the unusual C–C connection between both pyridinium moieties. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)