Stereocontrolled construction of 1, 7-dimethyl ABC [6.6. 6] tricycles. Part I. Transannular Diels-Alder reactions of 14-membered macrocycles containing trans- …

…, S Goldstein, P Deslongchamps

Index: Xu, Yao-Chang; Roughton, Andrew L.; Plante, Raymond; Goldstein, Solo; Deslongchamps, Pierre Canadian Journal of Chemistry, 1993 , vol. 71, # 8 p. 1152 - 1168

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Citation Number: 16

Abstract

Transannular Diels-Alder reactions of 14-membered macrocyclic trienes possessing a methyl substituent on both the diene and dienophile moiety have been investigated. Macrocyclic structures 1 a, 1 b, and 1 c having cis-trans-trans (CTT), trans-cis-trans (TCT), and trans-trans-trans (TTT) geometries could be stereoselectively constructed by coupling appropriately functionalized dienes 5 and dienophile 4 following an intramolecular ...