Isoquinolines. I. Preparation and Stereochemistry of 9, 10-Epoxy-1-(p-methoxybenzyl)-2-methyldecahydroisoquinolines

Abstract

Epoxidation of 1-(p-methoxybenzyl)-2-methyl-1, 2, 3, 4, 5, 6, 7, 8-octahydroisoquinoline (7) affords the two isomeric epoxides (14 and 15). Chemical evidence shows that performic acid exclusively attacks from the cis-side to the 1-substituent. The competitive reactions of 14 and 15 are qualitatively examined by gas chromatographic and thin-layer chromatographic analyses.