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01 (br s, 1H, H 16 ), 4.00?3.88 (m, 1H, H 5 ), 3.74 (s, 3H, H 13 or H 14 ), 3.67 (s, 3H, H 14 or H 13 ), p.2858 ,
4 Hz, J = 3.4 Hz and J = 0.5 Hz, 1H, p.24 ,
40 (ddd, apparent q, J = 3.6 Hz, 1H, H 1' ); 13 C NMR (100 MHz, D 6 -acetone) ? 176.0 (s, C 4 ), 149.7 (s, C 9 ), 148.6 (s, C 10, pp.130-135 ,
1 mL) (microwave irradiation, 150 °C, 1 h) After purification by flash chromatography on silica gel (petroleum ether, pp.95-95 ,
68 (s, 3H, H 12, p.67 ,
92 (m, 1H, H 1' ); 13 C NMR (100 MHz, D 6 -acetone) ? 176.3 (s, C 4 ), 160.6 (s, C 8 ), 141.4 (s, C 13 ), 139.0 (s, C 15 ,
H NMR (400 MHz, D 6 -acetone) ? 10.71 (br s, 1H, pp.606-152, 1114. ,
30 (dq, J = 8.3 Hz and J = 0.9 Hz, 1H ,
1 Hz, 1H, H 6 ), 7.08 (br s, 1H, H 10 ,
3 (s, C 3 ), 126.5 (d, C 6 ), C NMR (100 MHz EI?MS m/z (relative intensity) 188 (M +? , 63), pp.141-114 ,
84 (dd, J = 5.1 Hz and J = 341 (dtd, apparent dq, J = 3.4 Hz and J = 1, 5.96 (br s, 1H, H 12 ), 3.83 (ddd, J = 13.8 Hz, J = 9.7 Hz and J = 7.1 Hz, 1H, p.25, 2008. ,
13 C NMR (100 MHz, CDCl 3 ) ? 175.6 (s, C 4 ), 147.8 (s, C 9 ), 145.7 (s, C 10 ), 136.6 (s, C 17, pp.55-62, 2002. ,
CDCl 3 ) ? 7, 2H, H 18 ), 6.69 (s, 1H, H 11 ), 6.55 (s, 1H, H 8 ), 4.13 H NMR (400 MHz 18 ), 6.51 (s, 1H, H 8 ), 5.74 (s, 1H, pp.670-671, 1021. ,
); EI?MS m/z (relative intensity HRMS calcd for C 22, C NMR (100 MHz 2C, C 19 ), 125.8 (d, C 20 ), 124.7 (s, C 7 ), pp.228-213, 19581. ,
53 (s, 1H, H 8 ), 5.73 (s, 1H, pp.25-32, 1016. ,
03 (s, 1H (m, 1H, H 5 ), 3.83 (s, 3H, H 13 ), 3.53 (s, 3H, pp.4-24 ,
37 (d, AB syst, J = 13.3 Hz, 1H, H 16, pp.2705-2707 ,
0 (s, C 7 ) ,
0 Hz, 1H, H 5 ), 3.89 (s, 3H, H 12 or H 13, pp.84-90 ,
33 (dd, J = 12.8 Hz and J = 10.8 Hz, 1H, H 15, p.97 ,
(ddd, apparent br q, J = 4.3 Hz, 1H, H 1' ); 13 C NMR (100 MHz, p.81 ,
35 (br s, 1H, pp.31-38 ,
13 C NMR (100 MHz, CDCl 3 ) ? 175, pp.10-16 ,
0 (s, C 12 ); EI?MS m/z (relative intensity, pp.169-157 ,
57 (dd, J = 8.6 Hz and J = 2, pp.4-20 ,
CDCl 3 ) ? 175.8 (s, C 4 ), 158.5 (s, C 193 (s, C 7 ), 131.7 (d, 2C, C 17 ), 131.1 (s, C 12 ), 128.3 (s, C 16, MHz, vol.13, issue.122 1, pp.55-69 ,
1H, H 1' ); 13 C NMR (100 MHz, D 6 -DMSO) ? 173.8 (s, C 4 ), 137.1 (s, C 13 or C 1701 (s, C 17 or C 13 ), Hz, 1H, H 6 ), 2.44 (ddd, J = 15.2 Hz, J = 11.3 Hz and J = 6.0 Hz, 1H Hz and J = 4.3 Hz, 1H, H 1 ), ?0.09 (ddd, apparent br q, J = 4.2 Hz HRMS calcd for C 22 H 20 N 2 ONa (M+Na + ): 351.14678. Found, pp.20-21, 2018. ,
CDCl 3 ) ? 8.48 (br s, 1H, Mp = 202 °C; IR 3253 H NMR (400 MHz, pp.640-164, 1017. ,
29 (d, AB syst, J = 13.8 Hz, 1H, H 16, p.89 ,
70 (ddd, J = 15.9 Hz, J = 11.4 Hz and J = 6.5 Hz, 1H54 (ddd, apparent dd, J = 16.0 Hz and J = 4.3 Hz, 1H, p.10 ,
2 (s, C 7 or C 8 or C 13 or C 17 ), 136.1 (s, C 8 or C 13 or C 17 or C 7 ), 132.0 (s, C 13 or C 17 or C 7 or C 8 )1 (d, 2C, C 19 ), 126.7 (d, C 20 ), 124.4 (s, C 17 or C 7 or C 8 or C 13 ) ); EI?MS m/z (relative intensity, C NMR (100 MHz HRMS calcd for C 22 H 20 N 2 ONa (M+Na + ): 351.14678. Found, pp.238-144, 2002. ,
01 (d, J = 2.5 Hz, 1H, p.1 ,
1H, H 1' ); 13 C NMR (100 MHz, CDCl 3 ) ? 174, 0.77 (ddd, J = 8.4 Hz, J = 7.5 Hz and J = 4.9 Hz, pp.136-139 ,
84 (s, 3H, H 14 ), 3.79 (s, 3H, p.56 ,
21 (d, AB syst, J = 14.0 Hz, 1H, H 16 ,
55 (ddd, apparent td, J = 4.6 Hz and J = 3.2 Hz, 1H, H 1' ); 13 C NMR (100 MHz, CDCl 3 ) ? 177.7 (s, C 4 ), 159.4 (s, C 9 or C 11 ), 157.3 (s, C 11 or C 9 ), pp.71-114 ,
CDCl 3 ) ? 173.9 (s, C 4 ), 159.2 (s, C 9 or C 11, MHz, vol.157, issue.1367 ,
Hz and J = 1.1 Hz, 1H, H 11 ), 5.06 (s, 1H, OH) ,
54 (ddd, J = 13.1 Hz, J = 11.1 Hz and J = 5, p.22, 2006. ,
17 (d, AB syst, J = 13 C NMR (100 MHz, D 6 -acetone) ? 175.9 (s, C 5 ), Hz and J = 5.4 Hz, 1H 3.12 (m, 1H, H 1 ), 2.93 (d, AB syst, J = 13.4 Hz, 1H, H 17' ), 2.49?2.39 (m, 1H' ), 1.89 (m, 1H, H 4 ), 1.75 (m, 1H, 2003. ,
400 MHz, D 6 -acetone) ? 10.04 (br s, 1H, NH), 7.77 (m, 1H, H 10 ), 7.38 (ddd, apparent dt, J = 8.0 Hz and J = 1, Hz and J = 1.2 Hz, 1H, H 12 ), 7.03 (ddd, Mp > 104 °C (dec.); IR 3272 (br), pp.610-611, 1010. ,
41 (ddd, apparent dt, J = 8.0 Hz and J = 0, pp.1-7, 2015. ,
36 (dd, J = 5.5 Hz and J = 2.9 Hz, 1H, H 3 or H 4, p.73 ,
35 (ddd, J = 13.0 Hz, Hz and J = 5.4 Hz, 1H, H 8' ), 3.24 (d, AB syst, J = 13.4 Hz, 1H, pp.2-2 ,
1.27 (br d, J = 8.1 Hz, 1H, H 18' ); 13 C NMR (100 MHz, D 6 -acetone) ? 173 ,
0 (s, C 14 or C 189 (s, C 18 or C 148 (s, C 15 ), 131.0 (d, 2C, C 19 ) ,
12 (m, 2H, H 19 ), 4.30 (dd, J = 13.1 Hz and J = 5.6 Hz, 1H, H 6' ), 3.24 (ddd, apparent q, pp.71-73 ,
95 (ddd, apparent td, J = 8.6 Hz and J = 5, 3.06 (m, 1H, H 4 ), 3.02?2.93 (m, 2H, H 6' +H 7 ) 1H, H 2' ); 13 C NMR (100 MHz, CDCl 3 ) ? 177.8 (s, C 5 ), 159.5 (s, C 10 or C 12 ) HRMS calcd for C 22 H 23 NO 3 Na (M+Na + ): 372.15701. Found, pp.7-32 ,
5 (s, C 10 or C 12 ), 157.6 (s, C 12 or C 101 (s, C 17, 128.0 (d, 2C, C 19 ) 68.7 (s, C 16 ), pp.22-27 ,
68 (dd, J = 13.1 Hz and J = 6.5 Hz, 1H, pp.4836-4839 ,
9 (s, C 21 ), 136.5 (s, C 17, 130.7 (d, 2C, C 22 ), 128.7 (d, 2C, C 23 HRMS calcd for C 26 H 24 N 2 ONa (M+Na + ): 403.17808. Found, pp.45-51 ,
01 (s, 1H, NH), 4.52 (dd, J = 19.3 Hz and J = 370 (dd, J = 1926 (dd, apparent br t, Hz and J = 2.2 Hz, 1H, H 8 ), 3.16 (dd, apparent br t, J = 4.4 Hz, 1H, H 2 ), 2.91 (d, AB syst, J = 14.5 Hz, 1H, H 20 ), 2.72 (d, AB syst, J = 14.4 Hz, 1H, H 20' ), 2.69 (ddd, J = 7.3 Hz, J = 5 0.88 (br d, J = 13.5 Hz, 1H, H 4' ); 13 C NMR (100 MHz, D 6 -DMSO) ? 176.0 (s, C 7 ) HRMS calcd for C 26 H 24 N 2 ONa (M+Na + ): 403.17808. Found: 403.17822, pp.6704-111, 2003. ,