Tetrahedron Letters

The cyanide-catalyzed conversion of β-formylmuconates into triglochinates: A useful biomimetic synthesis

MG Ettlinger, JW Jaroszewski

Index: Ettlinger, Martin G.; Jaroszewski, Jerzy W. Tetrahedron Letters, 1980 , vol. 21, p. 3503 - 3506

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Citation Number: 4

Abstract

Abstract Upon treatment with cyanide under slightly basic conditions, β-formyl-cis, cis- muconic acid and esters, prepared from vanillin, undergo a sequence of prototropic shifts equivalent to an internal redox process in which 1, 4-reduction of the diene system is blanaced by oxidation of the formyl group.