Research

Synthesis of (+)-Obtusenyne


Reference:

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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Official URL:

http://dx.doi.org/10.1002/chem.200701567

Abstract

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.

Details

Item Type Articles
CreatorsMak, 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.
DOI10.1002/chem.200701567
DepartmentsFaculty of Science > Chemistry
RefereedYes
StatusPublished
ID Code27166

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