Aspects of the intramolecular Diels-Alder reactions of some 1, 3, 9-trienic amides, amines, and esters. An approach to the pentacyclic skeleton of the yohimboid …

SF Martin, SA Williamson, RP Gist…

Index: Martin, Stephen F.; Williamson, Sidney A.; Gist, R. P.; Smith, Karl M. Journal of Organic Chemistry, 1983 , vol. 48, # 26 p. 5170 - 5180

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Citation Number: 102

Abstract

The intramolecular cycloadditions of a number of 1, 3, 9-trienes containing an amide, amine, or ester function in the chain linking the dienophile and the diene were examined, and a general preference for the formation of cis cycloadducts was observed. Thus, the aza trienes 7b-h were found to undergo intramolecular Diels-Alder reaction upon thermolysis at temperatures ranging from 25 to 275" C to give mixtures of the cis-and trans- ...