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

• Published in: Tetrahedron letters 1999-04, Vol.40 (16), p.3255-3258
• Main Authors: Smelt, Kathryn H., Blériot, Yves, Biggadike, Keith, Lynn, Sean, Lane, Alexandra L., Watkin, David J., Fleet, George W.J.
• Format: Article
• Language: English
• ISSN: 0040-4039; 1873-3581
• 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 crystallography. 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 isomeric 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. Bromination of the peracetate 1 gives 2 which with sodium azide gives 3. Nucleophilic displacement of the bromide 2 or acylation of the amine 4 should permit the formation of libraries of rigid fucose mimics.