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Molecules 1999, 4(1), 1-12; doi:10.3390/40100001

A Straightforward Route to Enantiopure Pyrrolizidines and Indolizidines by Cycloaddition to Pyrroline N-Oxides Derived from the Chiral Pool

Centro di Studio C.N.R. sulla Chimica e la Struttura dei Composti Eterociclici e loro Applicazioni (CSCEA), Dipartimento di Chimica organica "Ugo Schiff", Università di Firenze, via G. Capponi 9, I- 50121 Firenze, Italy
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Received: 29 October 1997 / Accepted: 30 March 1998 / Published: 22 December 1998
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Abstract

Enantiomerically pure, five membered cyclic nitrones, easily obtained in large amounts from protected hydroxyacids and aminoacids such as D- and L-tartaric, L-malic, and L-aspartic acids, give cycloaddition reactions with a good diastereocontrol. The adducts of L-malic and L-aspartic acids derived from addition of nitrones to dimethyl maleate and g-crotonolactone were easily converted into enantiopure pyrrolizidinones, which can be transformed into polyhydroxypyrrolidines or polyhydroxypyrrolizidines, both interesting compounds as potential glycosidase inhibitors. The method is suitable for natural products synthesis as exemplified by a straightforward and convenient access to the pyrrolizidine alkaloid necine base (–)-hastanecine, as well as to indolizidine alkaloids, i.e. (+)- lentiginosine.
Keywords: Pyrrolizidines; pyrrolidines; stereoselective cycloaddition; glycosidase inhibitors; cyclic nitrones; review Pyrrolizidines; pyrrolidines; stereoselective cycloaddition; glycosidase inhibitors; cyclic nitrones; review
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Goti, A.; Cicchi, S.; Cordero, F.M.; Fedi, V.; Brandi, A. A Straightforward Route to Enantiopure Pyrrolizidines and Indolizidines by Cycloaddition to Pyrroline N-Oxides Derived from the Chiral Pool. Molecules 1999, 4, 1-12.

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