A Concise Total Synthesis of S-(+)-Tylophorine
被引量：1
A Concise Total Synthesis of S-(+)-Tylophorine
摘要
A highly efficient total synthesis of S-(+)-tylophorine has been accomplished in fully asymmetric fashion.
参考文献6
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1[1]T. An, R. Huang, Z. Yang, D. Zhang, G. Li, Y. Yao, J. Gao, Phytochemistry, 2001, 58, 1267.
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2[2]For recent reviews, see: Z. Li, Z. Jin, R. Huang, Synthesis, 2001, 2365. For recent synthesis of tylophorine also see: (a) D. L. Comins, L. A. Morgan, Tetrahedron Lett., 1991, 32, 5919. (b)W. H. Pearson, R. Walavalkar, Tetrahedron Lett., 1994, 50, 12293. (c) M. A. Ciufolini, F.Roschangar, J. Am. Chem. Soc., 1996, 118, 12082. (d) D. L. Comins, X. Chen, L. A. Morgan,J. Org. Chem., 1997, 62, 7435.
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3[3]T. Simandan, M. B. Smith, Synth. Commun., 1996, 26, 1827.
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4[4]Amino alcohol 12 is extremely sensitive to light. All operations should carry out rapidly and avoid exposing to light.
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5[5]Analytic data for S-(+)-tylophorine 1: m.p. 288-290C (dec.), IR (KBr) 1620, 1540, 1515 cm-1;1HNMR (CDC13, 200 MHz) δ ppm 7.78 (s, 1H), 7.77 (s, 1H), 7.24 (s, 1H), 7.05 (s, 1H), 3.98(AB q,2H, J=15 Hz, △v= 220 Hz, δA 4.60, δB 3.65), 4.09 (s,3H), 4.07 (s,3H), 4.02 (s,3H), 4.00(s,3H), 3.43 (t, 1H, J=7.4), 3.36 (d, 1H, J=5.7 Hz), 2.89 (t, 1H, J＝12 Hz), 2.56-2.45 (m, 2H),2.17-2.10 (m, 1H), 2.05-1.80 (m, 3H). 13CNMR (CDC13, 75.5MHz) δ ppm 147.6, 147.5,125.1, 124.6, 123.2, 123.0, 122.6, 122.4, 103.6, 102.8, 102.5, 102.2, 59.2, 55.0, 54.8, 54.0,52.8, 32.5, 29.1, 28.7, 20.5; [α] 25D +74.9 (c 1.0, CHC13); MS (EI, 70eV) m/z 393.20 (M+),calcd. m/z=393.19, 324 (100%); Anal. calcd. for C24H27NO4 C, 73.26; H, 6.92; N 3.56; Found.C, 73.38; H, 6.60; N, 3.55.
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6[6]T.R. Govindachari, T. G. Rajagopalan, N. Viswanathan, J. Chem. Soc., Perkin Trans. 1, 1974,1161.
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