A versatile approach to oligostilbenoid natural products--synthesis of permethylated analogues of viniferifuran, malibatol A, and shoreaphenol.
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.
Kim
Ikyon
I
Medicinal Chemistry Research Center, Korea Research Institute of Chemical Technology, Daejeon, 305-600, Republic of Korea. ikyon@krict.re.kr
Choi
Jihyun
J
D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D001685:Biological Factors / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry*
D001572:Benzofurans; D001685:Biological Factors; D013267:Stilbenes; C111734:malibatol A