Synthesis and Biological Activities of the 3,5-Disubstituted Indolizidine Poison Frog Alkaloid 239Q and Its Congeners

[摘要]：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 alpha 4 beta 2 nicotinic acetylcholine receptors.

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