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

Wang Xu | Zendy; Tsuneki Hiroshi | Zendy; Urata Noriko | Zendy; Tezuka Yasuhiro | Zendy; Wada Tsutomu | Zendy; Sasaoka Toshiyasu | Zendy; Sakai Hideki | Zendy; Saporito Ralph A. | Zendy; Toyooka Naoki | Zendy

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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.

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