Synthesis of Functionalized Trienes and Regioselective Formation of Medium-Ring Lactones through Intramolecular Diels-Alder Reaction

…, J Maddaluno, C Prandi, P Venturello

Index: Deagostino, Annamaria; Maddaluno, Jacques; Prandi, Cristina; Venturello, Paolo Journal of Organic Chemistry, 1996 , vol. 61, # 21 p. 7597 - 7599

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Citation Number: 23

Abstract

The intramolecular Diels-Alder reaction1 has not been extensively applied to the synthesis of macrocyclic rings because of problems related to regio-and exo-endo selectivity. 2 In the course of studies3 that explored the reactivity of R, β-unsaturated acetals in the presence of an equimolar mixture of butyllithium and potassium tert-butoxide (Schlosser's reagent LICKOR), 4 we have developed a method to transform crotonaldehyde diethyl acetal and ...