First total synthesis of 1-O-beta-D-glucopyranosyl-5-deoxyadenophorine and its aglycon congener: determination of the absolute configuration.
The first total synthesis of the potent glycosidase inhibitors 1-O-beta-D-glucopyranosyl-5-deoxyadenophorine and its aglycon congener is described in respectively 13 steps (9% overall yield) and 9 steps (29% overall yield) from (R)-Garner aldehyde. The synthesis takes advantage of several key reactions including a diastereoselective allylation of a chiral imine, a stereoselective epoxidation, and a glycoside coupling. In addition this study established unambiguously the absolute configuration of the natural products.
Felpin
François-Xavier
FX
Laboratoire de Synthèse Organique, CNRS UMR 6513, Université de Nantes, Faculté des Sciences et des Techniques, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France.
Boubekeur
Kamal
K
Lebreton
Jacques
J
D002236:Carbohydrate Conformation; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D005944:Glucosamine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
C484616:1-O-beta-D-glucopyranosyl-5-deoxyadenophorine; C484615:5-deoxyadenophorine; D004791:Enzyme Inhibitors; D006026:Glycoside Hydrolases; D005944:Glucosamine