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SYNTHESIS AND CHARACTERIZATION OF ISOMERIC 2,5-DJMETHYL-6-PHENYL-3-CYCLOHEXENE-1-METHANOL ANALOGS

Few if any reactions can rival the Diels-Alder cycloaddition for the construction of carbocyclic molecules. The stereochemical outcome for as many as four contiguous ring centers can usually be predicted due to the highly organized nature of the transition state. During the course of one of our programs several 2,5-dimethyl-6-phenyl-3-cyclohexene1-methanol isomers were required as key intermediates. Retrosynthetic evaluation of these compounds led us to choose the Diels-Alder reaction for their syntheses. Although the Diels-Alder reaction has been systematically studied for a wide variety of dienes and dienophiles, cinnamates have surprisingly received little attention, especially in reactions with hexadiene derivatives. We are aware of only two papers where cinnamic acids are condensed with trans,truns-2,4-hexadiene and in both cases, the cycloxexene ring was subsequently aromatized. I.'