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Nitrone dipolar cycloaddition routes to piperidines and indolizidines part 10 - Investigation of conjugate addition/intramolecular nitrone dipolar cycloadditions and their use in the synthesis of dendrobatid alkaloid precursors


Reference:

Horsley, H. T., Holmes, A. B., Davies, J. E., Goodman, J. M., Silva, M. A., Pascu, S. I. and Collins, I., 2004. Nitrone dipolar cycloaddition routes to piperidines and indolizidines part 10 - Investigation of conjugate addition/intramolecular nitrone dipolar cycloadditions and their use in the synthesis of dendrobatid alkaloid precursors. Organic and Biomolecular Chemistry, 2 (8), pp. 1258-1265.

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Official URL:

http://dx.doi.org/10.1039/b402307b

Abstract

The sequential intramolecular conjugate addition of the oxime 13 followed by intramolecular dipolar cycloaddition of the intermediate nitrone 14 affords a mixture of the isoxazolidines 15, 16 and 17. The tricyclic 6,5,5-adduct 15 is believed to be the product of kinetic control and can be equilibrated with the epimeric tricyclic 6,5,5-isoxazolidine 17 through a beta-elimination/conjugate addition process. Conditions have been developed for the two-step conversion of the ketone 12 under thermodynamic control into the racemic tricyclic 6,6,5-adduct 16 which is the core precursor of all the known histrionicotoxin alkaloids.

Details

Item Type Articles
CreatorsHorsley, H. T., Holmes, A. B., Davies, J. E., Goodman, J. M., Silva, M. A., Pascu, S. I. and Collins, I.
DOI10.1039/b402307b
DepartmentsFaculty of Science > Chemistry
RefereedYes
StatusPublished
ID Code27344

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