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Note | Regular issue | Vol 55, No. 10, 2001, pp.1987-1992
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9310
Regioselective Intramolecular Cycloaddition of C-(1-Acryloyl-2-pyrrolyl)-N-benzylnitrone: Entry to 6-Hydroxy-5-oxoindolizidines

Gianluigi Broggini,* Tullio Pilati, Alberto Terraneo, and Gaetano Zecchi

*Dipartimento di Scienze Chimiche, Fisiche e Matematiche, Università dell’Insubria, via Valleggio 11, 22100 Como, Italy


The title nitrone underwent intramolecular cycloaddition in regioselective and stereoselective manner, giving one bridged-ring cycloadduct (4). Further elaboration of the latter led to 6-hydroxy-5-oxoindolizidine derivatives (5) and (6), which can be seen as useful intermediates in alkaloids synthesis.