Backbone rearrangements of methyl (-)-kaur-9(11)-en-19-oate and its epoxide: structures of two diterpenes of a new skeletal type |
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Authors: | Tatsuhiko Nakano A.C. Spinelli A. Martín A. Usubillaga Andrew T. McPhail Kay D. Onan |
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Affiliation: | Centro de Química, Instituto Venezolano de Investigaciones Científicas I.V.I.C.) Apartado 1827, Caracas, Venezuela;Instituto de Investigacíon Química, Facultad de Farmacia, Universidad de Los Andes, Apartado 143, Mérida, Venezuela;Paul M. Gross Chemical Laboratory, Duke University, Durham, North Carolina 27706, U.S.A. |
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Abstract: | cleavage of the epoxide () of methyl (-)-kaur-9(11)-en-19-oate () with boron trifluoride-ether in benzene and in acetic anhydride yielded () and (), respectively. On epoxidation with -chloroperbenzoic acid in the presence of -nitrosomethyl urea, () suffered a backbone rearrangement to form (). |
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