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Paper | Special issue | Vol 79, No. 1, 2009, pp.565-571
Published online, 16th October, 2008
DOI: 10.3987/COM-08-S(D)16
Synthesis, Determination of the Absolute Stereochemistry, and Evaluations at the Nicotinic Acetylcholine Receptors of a Hydroxyindolizidine Alkaloid from the Ant Myrmicaria melanogaster

Dejun Zhou, Naoki Toyooka,* Hideo Nemoto, Kaoru Yamaguchi, Hiroshi Tsuneki, Tsutomu Wada, Toshiyasu Sasaoka, Hideki Sakai, Yasuhiro Tezuka, Shigetoshi Kadota, Tappey H. Jones, H. Martin Garraffo, Thomas F. Spande, and John W. Daly

*Faculty of Pharmaceutical Sciences, Toyama University, 2630 Sugitani, Toyama, Toyama 930-0194, Japan

Abstract

The first chiral synthesis of new hydroxyindolizidine alkaloid (1) detected in the ant Myrmicaria melanogaster has been achieved, and its absolute stereochemistry was determined to be 3S, 5R, 8S, 9S by the present chiral synthesis.