Facile Synthesis of Isoamericanol and Isoamericanin A
Facile Synthesis of Isoamericanol and Isoamericanin A
摘要
A number of benzodioxane compounds were synthesized using the pal1adium-catalyzedetherification of aryl halides by employing triphenylphosphan ligand. This method was used askey step in the synthesis of isoamericanol A and isoamericanin A.
A number of benzodioxane compounds were synthesized using the pal1adium-catalyzedetherification of aryl halides by employing triphenylphosphan ligand. This method was used askey step in the synthesis of isoamericanol A and isoamericanin A.
参考文献7
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1[1]W.X. Gu, X. B. Jing, X. F. Pan, A. C. S. Chan, T. K. Yang, Tetrahedron Lett., 2000, 41,6079.
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3[3]For a review see: H. Feuer, J. Hooz, in Chemistry of the Ether Linkage; Patai, S., Ed., Wiley Interscience, New York, 1967, p. 445.
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4[4]For a review see: C. Paradisi, In comprehensive organic synthesis: Trost. B. M., Fleming, I.,Eds, Pergarhon Press: Oxford, 1991; Vol. 4, p 423.
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5[5]For a review see: J. Lindley, Tetrahedron, 1984, 40, 1433.
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6[6]Y. Fukuyama, T. Hasegawa, M. Toda, M. Kodama, H. Okazaki, Chem. Pharm. Bull., 1992,40(1), 252.9: white powder, m.p.: 155-157℃, 1H-NMR(500MHz, DMSO-d6, δ ppm) 6.96(d, 1H, J=2Hz,H-2′), 6.93(dd, 1H, J=2, 8Hz, H-6′), 6.87(d, 1H, J=8Hz, H-7′), 6.70(dd, 1H, J=8, 2Hz, H-6),6.42(d, 1H, J=16Hz, H-7), 6.20(dt, 1H, J=16, 5Hz, H-8), 4.81(d, 1H, J=8Hz, H-7), 4.07(t, 1H,J=12.3Hz, 5Hz, H-9′), 4.03(m, 1H, H-8), 3.51 and 3.32(dd, 2H, J=12.3, 5Hz, H-9).HRFABMS (m/z) 330.1143 (M+ C18H18O6) calcd. 330.1111, EI-MS (m/z)) 330, 166, 148, 123.All the spectra data are in good agreement with those of isoamericanol A in literature reported 6.
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7[7]T. hasegawa, Y. Fukuyama, Y. Asakawa, Chem. Lett., 1987, 329.10: yellow powder, m.p. 173-176℃; HRMS(m/z) 328.0931 (M+ C18H16O6) calcd. 328.0933,1H-NMR(400MHz, DMSO-d6, δ ppm) 9.53(d, 1H, J=7.6Hz,-CHO),7.52(d, 1H, J=16Hz, H-7′),6.70-7.30(m, 5H, Ar-H), 6.67(dd, 1H, J=16, 8Hz, H-8′), 4.85(d, 1H, J=8Hz, H-7), 4.14(m, 1H,H-8), 3.35 and 3.57(dd, 2H, J=12.3, 5Hz, H-9).All the spectra data are in good agreement with those of isoamericanin A in literature reported 7.
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