De novo asymmetric synthesis of two 5-amino-5,6-dideoxy-D-allose derivatives

Article abstract of DOI:10.1016/S0040-4039(00)77271-6

Diels-Alder cycloaddition of sorbic aldehyde derivative 9 and of sorbic acid 10 with the chiral chloro-nitroso dienophile 7 led with excellent regio- and diastereoselectivity to the chiral cycloadducts 11a and 12, respectively. Catalytic osmylation of their Bzl-derivatives 11b and 13b, followed by reductive cleavage of the N-O bonds, gave ultimately the chiral aminoallose derivatives D-5 and D-6 which are potential glycosidase inhibitors.