Asymmetric synthesis of (+)-1-deoxynojirimycin and (+)-castanospermine

• Asymmetric total syntheses of (+)-1-deoxynojirimycin (1) and (+)-castanospermine (2) are described. Starting from diene 3, the required absolute stereochemistry is introduced by an asymmetric hydroxylation followed by epoxidation. An intramolecular cyclization of amine 17 gives access to the corresponding tetrasubstituted piperidine 18, which is a precursor to compounds 1 and 2. (+)-Deoxynojirimicyn (1) was obtained in 36% yield over 11 steps from diene 3, while (+)-castanospermine (2) was achieved in 13% after 19 steps from the same starting material.

Keyword

amino alcohols

asymmetric synthesis

alkaloids

allylic 4-methoxybenzoates

castanospermine

dihydroxylation

deoxynojirimycin

derivatives

glucosidase

inhibition

Publication and Content Type

ref (subject category)

art (subject category)