Synthesis of an eight carbon homologue of α-homomannojirimycin via a bicyclic aminolactone
1998
Abstract A thermally induced intramolecular 1,3-dipolar cycloaddition of an azidoester and subsequent sodium cyanoborohydride reduction of the resulting bicyclic vinylogous urethane to give a bicyclic aminolactone allows access to an eight carbon homologue of α-homomannojirimycin which is a weak fucosidase inhibitor. Intermediates with both an α- and β-amino acid moiety are described and may be useful for incorporation of homopipecolic acids into novel peptide libraries.
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