Tetrahedron

Applications of the intramolecular diels-alder reactions of heterodienes to the syntheses of indole alkaloids

SF Martin, B Benage, SA Williamson, SP Brown

Index: Martin, Stephen F.; Benage, Brigitte; Williamson, Sidney A.; Brown, Stephen P. Tetrahedron, 1986 , vol. 42, # 11 p. 2903 - 2910

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Citation Number: 21

Abstract

A novel intramolecular Diels-Alder reaction involving the addition of an α, β-unsaturated aldehyde to an electron-deficient, dienophilic partner has been exploited as the key step in the development of a general entry to the heteroyohimboid and corynantheioid alkaloids. Thus, the thermal cyclization of the nitrogen-linked triene 11, which is readily available in eight steps from propargyl alcohol, proceeded smoothly to afford the cis-cycloadduct 20 in ...