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Communication | Regular issue | Vol 14, No. 1, 1980, pp.43-46
Published online, 1st January, 1970
DOI: 10.3987/R-1980-01-0043
A Synthesis of (±)-Laevigatin

Shinzo Kano,* Tsutomu Ebata, and Shiroshi Shibuya

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

Reduction of α-anilinomethyl-1,2-butenolides with diisobutylaluminium hydride yielded the corresponding 3-anilinomethylfurans. Hydrogenolysis of 3-anilinomethyl-5,6,7,8-tetrahydro-7-methylbenzo[b]furan over 10 % Pd-C afforded (±)-menthofuran. This synthetic way leading to 3-methylfuran derivatives was applied to a synthesis of (±)-laevigatin starting from 4,7-dimethyl-1-tetralone.