Photobromination of a bicyclic mimic of alpha-L-fucose; Components for a combinatorial library of rigid fucose analogues

Photobromination of a rigid bicyclic alpha-L-fucose analogue, affords a sin gle crystalline monobromide, the structure of which is confirmed by X-ray c rystallography. Displacement of this bromide with azide proceeds with inver sion to a single crystalline azide, which on reduction leads to an amine an d thence to a range of novel substituted rigid alpha-L-fucose derivatives. Hydrolysis of the bromide leads to two isomeric alcohols via an acetate mig ration. Both the bromide and amine may prove to be useful intermediates for the generation of libraries of mimics of L-fucose. (C) 1999 Elsevier Scien ce Ltd. All rights reserved.