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■ New Synthesis of Tetrahydrobenzodifurans by Iterative Coupling of Quinone Monoacetals with Alkene Nucleophiles

Tohru Kamitanaka, Hitoho Takamuro, Kazuyuki Shimizu, Yudai Aramaki, Toshifumi Dohi, and Yasuyuki Kita*

*College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga, 525-8577, Japan

Abstract

A new efficient synthetic strategy of tetrahydrobenzodifurans has been developed by the repetitive [3+2] couplings of quinone monoacetals with alkene nucleophiles. Both the symmetrical and unsymmetrical tetrahydrobenzodifurans can be easily synthesized by this continuous method by altering the type of alkenes. These tetrahydrobenzodifurans have also become a useful precursor of highly-substituted benzofurans by dehydrogenation.