A general synthesis of (2Z)-terpenoic acids

D Cahard, M Mammeri, JM Poirier, L Duhamel

Index: Cahard, Dominique; Mammeri, Malika; Poirier, Jean-Marie; Duhamel, Lucette Tetrahedron Letters, 2000 , vol. 41, # 19 p. 3619 - 3622

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Citation Number: 8

Abstract

A three-step synthesis of (2Z),(4E)-polyenic acids 6 is described. Condensation of aldehydes 1 with potassium prenal enolate led to dihydropyranols 3 which were oxidized into dihydropyrones 5, precursors of (2Z),(4E)-polyenic acids 6. The procedure was applied to a synthesis of 13-cis-retinoic acids from β-ionylidene acetaldehydes.