Nucleophilic additions to cyclic nitrones en route to iminocyclitols – Total Syntheses of DMDP, 6-deoxy-DMDP, DAB-1, CYB-3, Nectrisine and Radicamine B

Year: 2008

Authors: Merino P., Delso I., Tejero T., Cardona F., Marradi M., Faggi E., Parmeggiani C., Goti A.

Autors Affiliation: Laboratorio de Síntesis Asimétrica Departamento de Química Orgánica, Instituto de Ciencia de Materiales de Aragón Universidad de Zaragoza CSIC. E-50009. Zaragoza, Aragón, Spain; Dipartimento di Chimica Organica Ugo Schiff and HeteroBioLab, Università di Firenze, associated with ICCOM-CNR, via della Lastruccia 13, I-50019 Sesto Fiorentino (FI), Italy
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Abstract: Highly diastereoselective nucleophilic additions to cyclic nitrones derived from L-malic acid and D-arabinose have been used for the construction of enantiomerically pure poly-hydroxylated pyrrolidines. The synthetic Strategy adopted was based on an oxidation/reduction protocol involving hydroxyldmine/nitrone pairs and demonstrates the use of reagent- and substrate-derived stereocontrol. In most cases reactions took place with total diastereoselectivity and in quantitative yield, with no purification being necessary. By this strategy, 2-(hydroxymethyl)-, 2-(aminomethyl)-, and 2-aryl-polyhydroxylated pyrrolidines have been prepared with abundant configurational diversity. The use of appropriate substrates and reagents allowed for approaches to DMDP, 6-deoxy-DMDP, DAB-1, CYB-3, nectrisine and radicamine B. Several analogues of these compounds with inverted configuration at one or more stereocenters were also prepared. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

Journal/Review: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Volume: 2008 (179      Pages from: 2929  to: 2947

KeyWords: iminocyclitols; pyrrolidines; nitrones; nucleophilic addition; nitrogen heterocycles
DOI: 10.1002/ejoc.200800098

Citations: 128
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