Improved Syntheses of (+)-Lentiginosine and (1S,2S,7R,8aS)-Trihydroxyoctahydroindolizine by Butenol Cycloaddition to Enantiopure Protected Dihydroxy Pyrroline N-Oxides

(opens in new window) Buy Article (opens in new window) Permissions and Reprints (opens in new window) All articles of this category (opens in new window) The amyloglucosidases inhibitors (+)-lentiginosine (1) and (1 S ,2 S ,7 R ,8a S )-1,2,7-trihydroxyoctahydroindolizine (2) have been synthesized in high overall yield via nitrone cycloaddition to butenol employing an enantiomerically pure L-tartaric acid derived nitrone 5a . These syntheses profit of a highly regio- and stereoselective cycloaddition and provide the target compounds wit yields increased of an order of magnitude with respect to previous reports. polyhydroxyindolizidines - lentiginosine - glycosidases inhibitors - amyloglucosidase - enantiomerically pure cyclic nitrones