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Issue 8, 2004
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Investigation of conjugate addition/intramolecular nitrone dipolar cycloadditions and their use in the synthesis of dendrobatid alkaloid precursors

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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 β-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.

Graphical abstract: Investigation of conjugate addition/intramolecular nitrone dipolar cycloadditions and their use in the synthesis of dendrobatid alkaloid precursors

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Publication details

The article was received on 16 Feb 2004, accepted on 08 Mar 2004 and first published on 23 Mar 2004


Article type: Paper
DOI: 10.1039/B402307B
Citation: Org. Biomol. Chem., 2004,2, 1258-1265
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    Investigation of conjugate addition/intramolecular nitrone dipolar cycloadditions and their use in the synthesis of dendrobatid alkaloid precursors

    H. T. Horsley, A. B. Holmes, J. E. Davies, J. M. Goodman, M. A. Silva, S. I. Pascu and I. Collins, Org. Biomol. Chem., 2004, 2, 1258
    DOI: 10.1039/B402307B

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