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Paper | Special issue | Vol 79, No. 1, 2009, pp.1043-1060
Published online, 22nd December, 2008
DOI: 10.3987/COM-08-S(D)81
Catalytic Asymmetric Synthesis of Both Enantiomers of Pyrrolizidines 223H’, 239K’, 265H’, and 267H’ Found in Madagascan Frogs (Mantella) and Their Affinities for Nicotinic Acetylcholine Receptor

Yukako Saito, Seiki Takahashi, Nehad Azer, Amira T. Eldefrawi, Mohyee E. Eldefrawi, and Hiroki Takahata*

*Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan


The asymmetric synthesis of pyrrolizidines 223H’, 239K’, 265H’, and 267H’ has been achieved starting from 1,5-hexadiene via a common synthetic intermediate 5. The affinity of both enanthiomers of 14 for nicotinic acetylcholine receptor was evaluated.