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Synthesis and Biological Activities of the 3,5‐Disubstituted Indolizidine Poison Frog Alkaloid 239Q and Its Congeners
Author(s) -
Wang Xu,
Tsuneki Hiroshi,
Urata Noriko,
Tezuka Yasuhiro,
Wada Tsutomu,
Sasaoka Toshiyasu,
Sakai Hideki,
Saporito Ralph A.,
Toyooka Naoki
Publication year - 2012
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.201200974
Subject(s) - chemistry , indolizidine , quinolizidine , pyrrolidine , alkaloid , stereochemistry , toad , ecology , biology
The first total synthesis of the 3,5‐disubstituted indolizidine toad alkaloid 239Q from the known pyrrolidine 1 has been achieved, in seven steps with a 35 % overall yield. The relative stereochemistry of natural 239Q was determined unambiguously by comparison of GC‐FTIR spectra of synthetic material with the skin extracts of the toad Melanophryniscus cupreuscapularis . The C7 congeners at the 5‐position ( 12 and 13 ) showed strong antagonist activities on the α4β2 nicotinic acetylcholine receptors.