Transannular Diels-Alder reactions on 14-membered macrocyclic trienes. Part I: stereoselective syntheses of the macrocyclic trienes precursors

A Ndibwami, S Lamothe, D Guay…

Index: Ndibwami, Alexis; Lamothe, Serge; Guay, Daniel; Plante, Raymond; Soucy, Pierre; et al. Canadian Journal of Chemistry, 1993 , vol. 71, # 5 p. 695 - 713

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Citation Number: 21

Abstract

Transannular Diels-Alder reactions on 14-membered macrocycles containing properly located diene and methyl-substituted dienophile units lead to ABC [6.6. 6] tricycles related to steroids. To study the influence of the olefin and diene geometry on the stereochemical outcome of the Diels-Alder reaction it was necessary to prepare macrocyclic trienes of well- defined stereochemistry. Eight different types of macrocyclic trienes might be obtained by ...