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The First Total Synthesis of 16-Hydroxygeranylgeraniol

The First Total Synthesis of 16-Hydroxygeranylgeraniol
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出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2003年第3期249-250,共2页 中国化学快报(英文版)
基金 This work was financial supported by the National Natural Science Foundation of China (Grant No. 20072012) and the Special Research Grant for Doctoral Sites in Chinese Universities (Grant No. 20010730001).
关键词 Total synthesis 16-hydroxygeranylgeraniol diterpene. Total synthesis, 16-hydroxygeranylgeraniol, diterpene.
分类号 O [理学]
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参考文献5

  • 1[1]F. Bohlmann, A. Adler, J. Jakupouic, R. M. King, H. Robinson, Phytochemistry, 1982, 21, 1349.
  • 2[2]M. Unbriet, K. B. Sharpless, J. Am. Chem. Soc., 1977, 99, 5526.
  • 3[3]J. A. Marshall, R. C. Andrews, J. Org. Chem., 1985, 50, 1603.
  • 4[4]For a review see: C. Najera, M. Yus, Tetrahedron, 1999, 55, 10547.
  • 5[5]Spectral data: 5, IR (KBr): v 3463, 1736 cm-1; 1H NMR (400 MHz, CDCl3, δ ppm) 7.47-7.90 (m, 5 H, Ar-H), 4.9-5.4 (m, 4 H, 4 CH=), 4.61 (t, 1 H, J = 3.6 Hz), 4.50 (d, 2 H, J = 7.0 Hz, CH2O), 4.15 (d, 2 H, J = 6.8 Hz), 4.10 (d, 1 H, J = 12.4 Hz), 3.89 (m, 1 H), 3.87 (d, 1 H, J = 12.4 Hz), 3.50 (m, 1 H), 2.04 (s, 3 H, CH3), 2.10-1.96 (m, 10 H, 5 CH2), 1.83-1.46 (m, 6 H, 3 CH2), 1.75 (s, 3 H, CH3), 1.71 (s, 3 H, CH3), 1.55 (s, 3 H, CH3), 1.52 (s, 3 H, CH3); EIMS, m/z: 429 (M+-SO2Ph, 5); 6, IR (KBr): 3432 cm-1; 1H NMR (400 MHz, CDCl3, δ ppm) 5.42 (t, 2 H, J = 6.4 Hz), 5.11 (t, 2 H, J = 6.4 Hz), 4.61 (t, 1H, J = 3.6 Hz), 4.15 (d, 2 H, J = 6.8 Hz), 4.10 (d, 1 H, J = 12.4 Hz), 3.89 (m, 1 H), 3.87 (d, 1 H, J = 12.4 Hz), 3.50 (m, 1 H), 2.13-2.00 (m, 12 H), 1.68 (s, 6 H), 1.66 (s, 3 H), 1.59 (s, 3 H), 1.70-1.53 (m, 6 H); EIMS, m/z: 288 (M+-DHP-OH, 15); 1, IR (KBr): 3328, 2933, 2870, 1669, 1057, 1006, 920 cm-1; 1H NMR (400 MHz, CDCl3, δ ppm) 5.39 (t, 2 H, J = 6.4 Hz), 5.11(t, 2 H, J = 6.4 Hz), 4.13 (d, 2 H, J = 6.4 Hz), 3.87 (s, 2 H), 2.13-2.00 (m, 12 H), 1.68 (s, 6 H), 1.66 (s, 3 H), 1.59 (s, 3 H); 13C NMR (100 MHz, CDCl3, δ ppm) 139.5, 137.5, 135.4, 134.7, 126.0, 124.7, 123.8, 123.4, 68.9, 59.3, 42.8, 39.4, 36.8, 31.6, 26.2, 26.0, 25.4, 23.3, 20.8, 16.2; EIMS, m/z: 288 (M-18, 9); HRMS (ESI): M++Na, 329.2450. C20H34O2+Na requires M++Na 329.2451.

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