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Communication | Regular issue | Vol 12, No. 6, 1979, pp.791-793
Published online, 1st January, 1970
DOI: 10.3987/R-1979-06-0791
A Simple and Facile Total Synthesis of Sesquiterpene, Cuparene by Using Furan Derivatives

Tetsuji Kametani,* Masayoshi Tsubuki, and Hideo Nemoto

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

5-Methyl-2-(4-methylbenzyl)furan (4) obtained from the condensation of 2-lithio-5-methylfuran with 4-methylbenzyl bromide was converted into 3-methyl-2-(4-methylbenzyl) cyclopenten-2-one (6) via 1-(4-methylphenyl)-hexane-2,5-dione (5). 1,4-Addition of methyl group into 6 furnished 3,3-dimethyl-2-(4-methylphenyl)cyclopentanone (7). This result constitutes a formal total synthesis of cuparene (9).