The First Total Synthesis of 16-Hydroxygeranylgeraniol
The First Total Synthesis of 16-Hydroxygeranylgeraniol
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).
参考文献5
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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.
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4[4]For a review see: C. Najera, M. Yus, Tetrahedron, 1999, 55, 10547.
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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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