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

…, Y Tezuka, T Wada, T Sasaoka, H Sakai…

Index: Wang, Xu; Tsuneki, Hiroshi; Urata, Noriko; Tezuka, Yasuhiro; Wada, Tsutomu; Sasaoka, Toshiyasu; Sakai, Hideki; Saporito, Ralph A.; Toyooka, Naoki European Journal of Organic Chemistry, 2012 , # 36 p. 7082 - 7092

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Citation Number: 4

Abstract

Abstract 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 ...

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