Studies on hypolipidemic agents. I. Synthesis of 1,3-dioxolanes and 1,3-dioxanes.

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Abstract
2-Aryl-substituted 3a,4,5,9b-tetrahydronaphtho[1,2-d]-1,3-dioxolanes, 5-phenyl- 5-(1,2,3,4-tetrahydro-2-naphthyl)- and 5-(2-naphthyl)-1,3-dioxanes and 3-aryl-substituted 1H-naphtho[2,1-d][1,3]dioxins were synthesized. Among them, the 1,3-dioxanes were each obtained as a mixture of the trans and cis isomers. Two stereoisomers of the 2-(3-pyridyl)-substituted derivatives and the trans isomers of the other 1,3-dioxanes were isolated and their stereostructures are discussed. Most of the trans isomers of the 1,3-dioxanes showed potent hypolipidemic activity in rats, while the cis isomers were inactive. The most active compound was trans-5-(6-methoxy-1,2,3,4-tetrahydro-2-naphthyl)-2-(3-pyridyl)-1,3-dioxane.

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