Novel Route to L-Hexoses from L-Ascorbic Acid: Asymmetric Synthesis of L-Galactopyranose and L-Talopyranose Preliminary Communication

✍ Scribed by Ludmila Ermolenko; N. André Sasaki; Pierre Potier

• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: German
• Weight: 112 KB
• Volume: 86
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200390302

✦ Synopsis

Abstract

A novel route with L‐ascorbic acid as a single common starting material to asymmetric synthesis of all eight diastereomers of L‐hexoses is described. Assessment of this new approach is demonstrated by the expedient synthesis of L‐galactopyranose and L‐talopyranose derivatives. Key steps involve stereoselective preparation of chiral (E)‐ and (Z)‐γ‐hydroxy‐α,β‐unsaturated esters and their stereo‐controlled dihydroxylation by OsO~4~.