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Communication | Regular issue | Vol 24, No. 7, 1986, pp.1835-1839
Published online, 1st January, 1970
DOI: 10.3987/R-1986-07-1835
The High Pressure Mediated Reaction of π-Excessive Heterocycles with Maleic Anhydride Derivatives: A Synthetic Approach to Cantharidibn Analogues

Kiyoshi Matsumoto,* Shiro Hashimoto, Yukio Ikemi, Shinichi Otani, and Takane Uchida

*Graduate School of Human and Environmental Studies, Kyoto University, Yoshida-Nihonmatsu-cho, Sakyo-ku, Kyoto 606-8501, Japan

Abstract

High pressure mediated Diels-Alder reactions of 3,4-dimethoxyfuran with cyclohexene-1,2-dicarboxylic anhydrides and cyclopentene-1,2-dicarboxylic anhydride followed by catalytic hydrogenstion produced 11-oxatricyclo[6.2.1.02,7]undecane-endo-2,7dicarboxylic anhydrides and 10-oxatricyclo[5.2.1.02,6]decane-endo-2,6-dicarboxylic anhydride albeit in low yields. Reactions of N-methylpyrrole and pyrrole with dichloromaleic anhydride at high pressure resulted in Friedel-Crafts type of acylation.