Synthesis of (+)-Obtusenyne
Mak, S. Y. F., Curtis, N. R., Payne, A. N., Congreve, M. S., Wildsmith, A. J., Francis, C. L., Davies, J. E., Pascu, S. I., Burton, J. W. and Holmes, A. B., 2008. Synthesis of (+)-Obtusenyne. Chemistry - A European Journal, 14 (9), pp. 2867-2885.
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An enantioselective synthesis of the halogenated medium-ring ether natural product (+)-obtusenyne is reported which uses the ring expansion of a seven-membered ketene acetal by means of a Claisen rearrangement to construct the core nine-membered oxygen heterocycle. The trans substituents across the ether linkage were established by using a transition-metalcatalyzed intramolecular hydrosilation reaction of an exo-cyclic enol ether. In addition, a formal synthesis of ent-obtusenyne from 2-deoxy-D-ribose is reported. A number of interesting points regarding the chemistry of medium-ring oxygen heterocycles are highlighted.
|Creators||Mak, S. Y. F., Curtis, N. R., Payne, A. N., Congreve, M. S., Wildsmith, A. J., Francis, C. L., Davies, J. E., Pascu, S. I., Burton, J. W. and Holmes, A. B.|
|Departments||Faculty of Science > Chemistry|
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