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

H T Horsley, A B Holmes, J E Davies, J M Goodman, M A Silva, Sofia I Pascu, I Collins

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27 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)1258-1265
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume2
Issue number8
DOIs
Publication statusPublished - 2004

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