Organometallic Reactions in Carbohydrate Chemistry (Orgmet. Carb.)
Organometallic Reactions in Carbohydrate Chemistry
Start date: Feb 15, 2008,
End date: Jan 14, 2010
The aim of this project is to apply some state of the art transition metal catalysed reactions to carbohydrate systems. We plan to investigate the possibilities of using transition metals to catalyse C-C fond forming cyclisations and C-N bond forming cyclisation and cross-coupling reactions. In carbocyclisation reactions, we will be focussing on ene-yne systems, which will be synthesised from carbohydrate starting materials. Electrophilic transition metal complexes such as gold complexes can induce cyclisation of an alkene onto an activated alkyne. Alternatively, debenzylative etherification may be favoured. Ruthenium complexes can carry out one-pot oxidation-reductive-amination to form secondary amines from primary amines and alcohols. We plan to apply this reaction to the synthesis of amine-linked disaccharides, and also to cyclisation reactions where a carbohydrate-derived diol can cyclise with a primary amine, giving an N-substituted iminosugar or azasugar. A combination approach where alkene and alkyne functionalities are introduced to a molecule by the amine coupling reaction followed by a carbocyclisation will be investigated. The polyhydroxylated products of these reactions will be new or known glycomimetics. The new compounds will be tested for their biological activity by our collaborators.
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