Tetrahedron letters

A tandem synthesis of (±)-euphococcinine and (±)-adaline

EC Davison, AB Holmes, IT Forbes

Index: Davison, Edwin C.; Holmes, Andrew B.; Forbes, Ian T. Tetrahedron Letters, 1995 , vol. 36, # 49 p. 9047 - 9050

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Citation Number: 29

Abstract

Intramolecular hydroxylamine-alkyne cyclisation of the hydroxylamines 8 and 9 afforded six- membered cyclic nitrones which without isolation underwent a tandem intramolecular dipolar cycloaddition to produce the tricyclic isoxazolidines 6 and 7 respectively. These were converted in two steps into the ladybird defence alkaloids (±)-euphococcinine 4 and (±)- adaline 5.