Diastereoselective formation of a quaternary center in a pyroglutamate derivative. Formal synthesis of Monatin

✍ Scribed by Davi de Jesus Oliveira; Fernando Coelho

• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 216 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)01401-0

✦ Synopsis

In this communication we describe a highly diastereoselective formation of a quaternary center present in the structure of Monatin, a potent sweetening agent isolated from natural sources. The synthesis of a derivative useful for biological studies on the interactions of this type of sweetening substance on taste receptors is described. The strategy relies on the oxidation of an enolate originating from a pyroglutamate derivative followed by a highly diastereoselective alkylation with an electrophile obtained from indole.