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Organic & Biomolecular Chemistry

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Paper

Org. Biomol. Chem., 2009, 7, 2788 - 2795, DOI: 10.1039/b901911a


A versatile approach to oligostilbenoid natural products – synthesis of permethylated analogues of viniferifuran, malibatol A, and shoreaphenol

Ikyon Kim and Jihyun Choi


A highly practical route to oligostilbenoid natural products is described. A regioselective Bi(OTf)3-catalyzed cyclodehydration provided ready access to 3-arylbenzofuran. Pd-catalyzed direct C–H activation of benzofuran and subsequent cross-coupling with aryl halide was successfully implemented for the introduction of aryl group at the C2 position of benzofuran. Further manipulation of the 2,3-diarylbenzofuran led to the efficient total synthesis of permethylated analogues of viniferifuran, malibatol A, and shoreaphenol.

Graphical abstract image for this article  (ID: b901911a)