Bridged Lactones and Bridged Carbocyclic Systems from 2-(3, 4, 5-Trimethoxyphenyl)-4, 5-dimethyl-Δ4-cyclohexenecarboxylic Acid. Novel Mescaline Analogs1

TJ Perun, L Zeftel, RG Nelb…

Index: Perun,T.J. et al. Journal of Organic Chemistry, 1963 , vol. 28, # 11 p. 2937 - 2943

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Citation Number: 4

Abstract

Treatment of 2-(3, 4, 5-trimethoxyphenyl)-4, 5-dimethyl-A4-cyclohexenecarboxylic acid (C) with methanesulfonic acid yielded a mixture of the y-and &lactones II and E, and a mixture of bridged ring acids, consisting principally of trimethoxybenzodimethyl [2.2. 2] bicyclooctanecarboxylic acid (F). The structure of F was established by conversion of the amine F-5 (which is a mescaline analog of unusual type), degradation of the amine vsa ...