1240894-19-2Relevant academic research and scientific papers
Rapid access to jaspine B and its enantiomer
Santos, Cécile,Fabing, Isabelle,Saffon, Nathalie,Ballereau, Stéphanie,Génisson, Yves
, p. 7227 - 7233 (2013/08/23)
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.
Flexible and enantioselective access to jaspine B and biologically active chain-modified analogues thereof
Salma, Yahya,Ballereau, Stephanietlse,Maaliki, Carine,Ladeira, Sonia,Andrieu-Abadie, Nathalie,Genisson, Yves
experimental part, p. 3227 - 3243 (2010/08/21)
Whereas the all-cis tetrahydrofuran framework of the cytotoxic anhydrophytosphingosine jaspine B is considered as a relevant pharmacophore, little is known about the influence of the aliphatic chain of this amphiphilic molecule on its activity. We develop
