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Communication | Regular issue | Vol 65, No. 1, 2005, pp.5-8
Published online, 29th November, 2004
DOI: 10.3987/COM-04-10269
Enantioselective Synthesis of Poison-Frog Alkaloid 237D and Determination of Absolute Stereochemistry

Naoki Toyooka,* Masashi Kawasaki, Hideo Nemoto,* John W. Daly, Thomas F. Spande, and H. Martin Garraffo

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

Abstract

An enantioselective synthesis of the 5-heptyl-8-methylindolizidine ((-)-7) has been achieved. Alkaloid ((-)-7, (MW 237)) was used to determine the relative and absolute stereochemistry of the natural indolizidine 237D from frog skin as 5S, 8S, 9R using GC-IR and GC-MS. Chiral gas-chromatographic comparisons with catalytically reduced (+)-235B” and (-)-235B’ indicated (-)-7 had the same absolute stereochemistry as the dihydro-product resulting from (-)-235B’ and is naturally occurring in certain extracts of Panamanian poison frogs (Dendrobates).