Stereoselective synthesis of five and/or six membered ring hydroxylactones obtained by Lewis acid mediated reaction of γ,δ-epoxy-β-hydroxyesters; access to 5-methylated 2-deoxysugars.

✍ Scribed by Kassoum Nacro; Michel Baltas; Jean-Marc Escudier; Liliane Gorrichon

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 1010 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(96)00998-2

✦ Synopsis

A stereoselective route to six and/or five membered ring lactones from optically active y,& epoxy-P-hydroxyesters obtained from nerol and geraniol has been developed. The intramolecular cyclization by epoxide ring opening occurred via activation of 6-endo over the usually favoured 5-exe, and the application of this technology to the stereocontrolled synthesis of 5-methylated 2-deoxysugars was achieved.