Nitrone dipolar cycloaddition routes to piperidines and indolizidines. Part 9. Formal synthesis of (−)-pinidine and total synthesis of (−)-histrionicotoxin,(+)- …

…, JE Davies, PR Raithby, JP Adams, IT Forbes…

Index: Davison, Edwin C.; Fox, Martin E.; Holmes, Andrew B.; Roughley, Stephen D.; Smith, Catherine J.; Williams, Geoffrey M.; Davies, John E.; Raithby, Paul R.; Adams, Joseph P.; Forbes, Ian T.; Press, Neil J.; Thompson, Mervyn J. Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 12 p. 1494 - 1514

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Citation Number: 37

Abstract

We have made extensive use of the intramolecular 1,3-dipolar cycloaddition of C- and N-alkenyl nitrones in the synthesis of alkaloids in recent years. 12–23 Our discovery of the tandem hydroxylamine-alkyne cyclisation to form cyclic nitrones which could be trapped by an intramolecular 1,3-dipolar cycloaddition of a pendant dipolarophile 14,22 led us to the design of the present approach to histrionicotoxin (Scheme 1). Thus cyclisation of the hydroxylamino-alkyne 5 ...