Tetrahedron

Sesquiterpene lactones: A total synthesis of (±) quadrone

JM Dewanckele, F Zutterman, M Vandewalle

Index: Dewanckele, J. M.; Zutterman, F.; Vandewalle, M. Tetrahedron, 1983 , vol. 39, # 20 p. 3235 - 3244

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Citation Number: 24

Abstract

Two routes towards (±) quadrone (1), via an intramolecular Diels-Alder reaction have been studied. The cycloaddition of 5 failed, probably because of prohibitive strain. In the alternative approach, the key step afforded a mixture of the endo-and exo-adducts 6 and 7. Both isomers were transformed into Danishefsky's intermediate 2, which has previously been converted to the title compound 1.