Santos C.,LSPCMIB |
Fabing I.,LSPCMIB |
Saffon N.,CNRS Institute of Chemistry |
Ballereau S.,LSPCMIB |
Tetrahedron | Year: 2013
A rapid access to jaspine B and its enantiomer ent-jaspine B from a 2,3-aziridino-γ-lactone is reported. This synthesis relies on a one pot regioselective aziridine ring-opening followed by intramolecular cyclization to install the cis-amino-alcohol pattern of jaspine B and on a modified Julia olefination of the lactone followed by a diastereoselective hydrogenation for the introduction of the C14 aliphatic chain. The separation of enantiomers in the course of this synthesis was achieved by supercritical fluid chromatography. The cytotoxicity of both enantiomers was evaluated. © 2013 Elsevier Ltd. All rights reserved.