Photobromination of a bicyclic mimic of α-L-fucose; components for a combinatorial library of rigid fucose analogues

Article abstract of DOI:10.1016/S0040-4039(99)00377-9

Photobromination of a rigid bicyclic α-L-fucose analogue, affords a single crystalline monobromide, the structure of which is confirmed by X-ray cvystallography. Displacement of this bromide with azide proceeds with inversion to a single crystalline azide, which on reduction leads to an amine and thence to a range of novel substituted rigid α-L-fucose derivatives. Hydrolysis of the bromide leads to two isomenc alcohols via an acetate migration. Both the bromide and amine may prove to be useful intermediates for the generation of libraries of mimics of L-fucose.