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

Ikyon Kim; Jihyun Choi

doi:10.1039/B901911A

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Organic & Biomolecular Chemistry

Issue 13, 2009

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

Ikyon Kim and Jihyun Choi

Org. Biomol. Chem., 2009, 7, 2788-2795

DOI: 10.1039/B901911A
Received 29 Jan 2009, Accepted 03 Apr 2009
First published on the web 21 May 2009

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Abstract
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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.

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Organic & Biomolecular Chemistry

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

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