Carbonylative lactonization via carbonyl oxygen attack: a short and selective total synthesis of uncinine and its analogues

H Fáková, M Pour, J Kuneš, P Šenel

Index: Fakova, Helena; Pour, Milan; Kunes, Jiri; Senel, Petr Tetrahedron Letters, 2005 , vol. 46, # 47 p. 8137 - 8140

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Citation Number: 13

Abstract

A novel cytotoxic butenolide alkaloid, uncinine, has been synthesized for the first time in 8 steps from propargyl alcohol. The sequence features a mild and efficient tandem carbonylative lactonization of a β-iodoenone precursor using an inorganic base at 1atm CO, and an indirect attachment of the pyrrolidinone ring via nucleophilic substitution with methyl γ-aminobutyrate.