Synthesis of (+)-Obtusenyne

S Y Frankie Mak, Neil R Curtis, Andrew N Payne, Miles S Congreve, Andrew J Wildsmith, Craig L Francis, John E Davies, Sofia I Pascu, Jonathan W Burton, Andrew B Holmes

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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.
Original languageEnglish
Pages (from-to)2867-2885
Number of pages19
JournalChemistry - A European Journal
Volume14
Issue number9
DOIs
Publication statusPublished - 17 Mar 2008

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    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., & Holmes, A. B. (2008). Synthesis of (+)-Obtusenyne. Chemistry - A European Journal, 14(9), 2867-2885. https://doi.org/10.1002/chem.200701567