Diastereoselective synthesis of all eight l-hexoses from L-ascorbic acid.
[reaction: see text] A novel versatile method for the synthesis of all eight diastereomerically pure L-hexoses was developed. L-Ascorbic acid was converted to two diastereomers A. These alpha-hydroxy esters were transformed into four gamma-alkoxy-alpha,beta-unsaturated esters C via the intermediates B and subsequent Wittig olefination reactions. Each one of compounds C was subjected to dihydroxylation to provide a set of two diols D. Anti/syn-differentiation in diol formation was manipulated by using (DHQD)2PHAL and (DHQ)2PHAL as chiral ligands. Further two-step reaction sequence affords all eight diastereopure L-hexoses.
Ermolenko
Ludmila
L
Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
Sasaki
N André
NA
D001205:Ascorbic Acid; D006601:Hexoses / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
D006601:Hexoses; D007202:Indicators and Reagents; D001205:Ascorbic Acid