675130-54-8Relevant articles and documents
First total synthesis of (+)-adenophorine, a naturally occurring inhibitor of glycosidases
Pearson, Morwenna S. M.,Evain, Michel,Mathe-Allainmat, Monique,Lebreton, Jacques
, p. 4888 - 4894 (2008/03/14)
The first total synthesis of a naturally occurring iminosugar, (+)-adenophorine, in 14 steps from the (+)-enantiomer of Garner's aldehyde, is reported. The strategy is based on the preparation and functionalization of enantiomerically pure trans-6-ethyl-2
First Total Synthesis of 1-O-β-D-Glucopyranosyl-5-deoxyadenophorine and Its Aglycon Congener: Determination of the Absolute Configuration
Felpin, Francois-Xavier,Boubekeur, Kamal,Lebreton, Jacques
, p. 1497 - 1503 (2007/10/03)
The first total synthesis of the potent glycosidase inhibitors 1-O-β-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.