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.
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.
François-Xavier
FX
Felpin
Kamal
K
Boubekeur
Jacques
J
Lebreton
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