supporting information ·

S1

Supporting Information

Novel Total Syntheses of Oxoaporphine Alkaloids Enabled by Mild

Cu-Catalyzed Tandem Oxidation/Aromatization of 1-Bn-DHIQs

Bo Zheng, Hui-Ya Qu, Tian-Zhuo Meng, Xia Lu, Jie Zheng, Yun-Gang He, Qi-Qi Fan, Xiao-Xin Shi*

Shanghai Key Laboratory of Chemical Biology and Department of Pharmaceutical Engineering, School of

Pharmacy, East China University of Science and Technology, 130 Mei-Long Road, Shanghai 200237, P. R. China

E-mail: [email protected]

Contents1H and 13C NMR Spectra of All Compounds..........................................................................S2-S45

Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2018

mailto:[email protected]

S2

1H and 13C NMR Spectra of All Compounds: 1H NMR (CDCl3, 400 MHz) spectrum of compound 2a:

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)

2.02

1.01

1.00

1.01

1.00

1.00

2428

.32

2747

.50

2755

.54

2800

.62

2802

.33

2829

.93

2831

.69

2837

.97

2839

.71

2984

.18

2997

.73

3164

.52

3178

.05 NAME sx-zb-002

EXPNO 10PROCNO 1Date_ 20180129Time 14.31INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 0SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 203DW 60.800 usecDE 6.50 usecTE 292.5 KD1 1.00000000 secTD0 1

======== CHANNEL f1 ========NUC1 1HP1 14.75 usecPL1 -1.00 dBPL1W 13.37643433 WSFO1 400.1324710 MHzSI 32768SF 400.1300062 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00

13C NMR (CDCl3, 100 MHz) spectrum of compound 2a:

0102030405060708090100110120130140150160170180190f1 (ppm)

102.

1010

6.98

109.

08

124.

1812

6.69

135.

3713

9.13

148.

7715

1.39

NAME sx-zb-002EXPNO 10PROCNO 1Date_ 20180130Time 21.13INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zgpg30TD 65536SOLVENT CDCl3NS 400DS 0SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 203DW 20.800 usecDE 6.50 usecTE 293.5 KD1 2.00000000 secD11 0.03000000 secTD0 1

======== CHANNEL f1 ========NUC1 13CP1 9.85 usecPL1 -2.20 dBPL1W 60.02919006 WSFO1 100.6228298 MHz

======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL2 -1.00 dBPL12 14.71 dBPL13 17.90 dBPL2W 13.37643433 WPL12W 0.35920334 WPL13W 0.17232187 WSFO2 400.1316005 MHzSI 32768SF 100.6127690 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40

NO2O

O2a

NO2O

O2a

S3

1H NMR (CDCl3, 400 MHz) spectrum of compound 2b:

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)

2.93

2.93

1.01

1.01

1.01

1.01

1.00

1573

.32

1579

.11

2766

.62

2774

.96

2810

.83

2812

.85

2869

.03

2871

.06

2877

.34

2879

.35

3015

.65

3029

.21

3180

.09

3193

.69

NAME sx-zb-001EXPNO 10PROCNO 1Date_ 20180129Time 14.25INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 0SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 57DW 60.800 usecDE 6.50 usecTE 292.5 KD1 1.00000000 secTD0 1


13C NMR (CDCl3, 100 MHz) spectrum of compound 2b:

0102030405060708090100110120130140150160170180190200

f1 (ppm)

56.0

256

.10

110.

1811

1.30

122.

7812

4.71

135.

1313

9.39

149.

5115

2.78 NAME sx-zb-001

EXPNO 10PROCNO 1Date_ 20180130Time 20.34INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zgpg30TD 65536SOLVENT CDCl3NS 400DS 0SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 203DW 20.800 usecDE 6.50 usecTE 293.4 KD1 2.00000000 secD11 0.03000000 secTD0 1



NO2MeO

MeO 2b

NO2MeO

MeO 2b

S4

1H NMR (CDCl3, 400 MHz) spectrum of compound 2c:

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)

3.01

3.00

3.02

1.04

1.00

1.01

1.00

1552

.58

1573

.16

1598

.86

2688

.90

2697

.66

2881

.48

2890

.24

3102

.40

3115

.99

3229

.06

3242

.66

NAME sx-wjj-101EXPNO 10PROCNO 1Date_ 20160330Time 10.09INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 0SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 90.5DW 60.800 usecDE 6.50 usecTE 295.6 KD1 1.00000000 secTD0 1


13C NMR (CDCl3, 100 MHz) spectrum of compound 2c:

0102030405060708090100110120130140150160170180190200

f1 (ppm)

56.2

060

.94

61.1

9

107.

68

117.

02

126.

65

135.

3713

6.52

142.

39

154.

2715

7.36 NAME sx-wjj-1010




OMeMeO

MeO

NO2

2c

OMeMeO

MeO

NO2

2c

S5

1H NMR (CDCl3, 400 MHz) spectrum of compound 3a:

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5

f1 (ppm)

2.06

1.92

1.70

1.93

0.99

1.00

1.00

626.17

1059.71

1066.43

1073.03

1160.88

1167.95

1175.26

2361.52

2365.21

2369.54

2375.79

2653.49

2655.12

2661.36

2662.97

2675.52

2677.14

2694.20

2697.94

2702.07

NAME sx-qhy-41

EXPNO 10

PROCNO 1

Date_ 20170519

Time 13.50

INSTRUM spect

PROBHD 5 mm PABBO BB-

PULPROG zg30

TD 65536

SOLVENT CDCl3

NS 16

DS 0

SWH 8223.685 Hz

FIDRES 0.125483 Hz

AQ 3.9846387 sec

RG 101

DW 60.800 usec

DE 6.50 usec

TE 295.8 K

D1 1.00000000 sec

TD0 1

======== CHANNEL f1 ========

NUC1 1H

P1 14.75 usec

PL1 -1.00 dB

PL1W 13.37643433 W

SFO1 400.1324710 MHz

SI 32768

SF 400.1300042 MHz

WDW EM

SSB 0

LB 0.30 Hz

GB 0

PC 1.00

13C NMR (CDCl3-TFA, 100 MHz) spectrum of compound 3a:

-100102030405060708090100110120130140150160170180190200210

f1 (ppm)

39.49

43.49

100.71

107.70

108.09

108.63

108.71

109.02

109.29

109.37

121.55

133.46

145.80

147.57

NAME sx-qhy-41

EXPNO 10

PROCNO 1

Date_ 20170524

Time 2.46

INSTRUM spect


PULPROG zgpg30

TD 65536

SOLVENT CDCl3

NS 400

DS 0

SWH 24038.461 Hz

FIDRES 0.366798 Hz

AQ 1.3631988 sec

RG 203

DW 20.800 usec

DE 6.50 usec

TE 297.0 K

D1 2.00000000 sec

D11 0.03000000 sec

TD0 1

======== CHANNEL f1 ========

NUC1 13C

P1 9.85 usec

PL1 -2.20 dB

PL1W 60.02919006 W

SFO1 100.6228298 MHz

======== CHANNEL f2 ========

CPDPRG2 waltz16

NUC2 1H

PCPD2 90.00 usec

PL2 -1.00 dB

PL12 14.71 dB

PL13 17.90 dB

PL2W 13.37643433 W

PL12W 0.35920334 W

PL13W 0.17232187 W

SFO2 400.1316005 MHz

SI 32768

SF 100.6127690 MHz

WDW EM

SSB 0

LB 1.00 Hz

GB 0

PC 1.40

O

O NH2

3a

O

O NH2

3a

S6

1H NMR (CDCl3, 400 MHz) spectrum of compound 3b:

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)

2.16

2.03

2.00

3.09

3.09

2.03

0.99

570.

65

1067

.07

1073

.88

1080

.71

1166

.60

1173

.38

1180

.27

1539

.24

1547

.06

2690

.95

2698

.16

2700

.15

2717

.91

2719

.14

2726

.42

NAME sx-zb-003EXPNO 10PROCNO 1Date_ 20180130Time 0.34INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 0SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 28.5DW 60.800 usecDE 6.50 usecTE 293.0 KD1 1.00000000 secTD0 1


13C NMR (CDCl3, 100 MHz) spectrum of compound 3b:

-100102030405060708090100110120130140150160170180190200210f1 (ppm)

39.5

143

.58

55.7

355

.83

111.

2211

1.96

120.

65

132.

35

147.

3414

8.81 NAME sx-zb-003




MeO

MeO 3bNH2

MeO

MeO 3bNH2

S7

1H NMR (CDCl3, 400 MHz) spectrum of compound 3c:

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)

2.12

2.04

2.02

3.17

3.09

3.07

1.04

1.00

928.

2510

77.3

510

84.3

410

91.3

411

55.5

211

62.5

511

69.5

3

1536

.37

1547

.88

1552

.42

2642

.22

2650

.68

2732

.75

2741

.20


======== CHANNEL f1 ========NUC1 1HP1 14.75 usecPL1 -1.00 dBPL1W 13.37643433 WSFO1 400.1324710 MHzSI 32768SF 400.1299943 MHzWDW EMSSB 0LB 0.30 HzGB 0

PC 1.00

13C NMR (CDCl3, 100 MHz) spectrum of compound 3c:

0102030405060708090100110120130140150160170180f1 (ppm)

33.8

4

42.8

1

55.9

760

.69

60.9

2

107.

16

124.

3512

5.46

142.

29

152.

0815

2.31 NAME sx-zb-719




OMeMeO

MeONH2

3c

OMeMeO

MeONH2

3c

S8

1H NMR (CDCl3, 400 MHz) spectrum of compound 4a:

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5

f1 (ppm)

2.06

2.08

2.02

0.86

2.11

2.06

1.03

2.03

1.03

1.00

1071.27

1078.08

1084.94

1373.44

1380.00

1386.38

1393.01

1516.32

2337.03

2369.82

2616.98

2618.73

2624.88

2626.61

2637.59

2639.30

2668.46

2672.32

2675.89

2680.23

2690.02

2973.37

2974.86

2980.85

2982.87

2990.69

3031.20

3032.58

3038.67

3039.63

3040.58

3046.26

3047.64

3207.51

3208.89

3215.75

3217.04

3218.92

NAME sx-qhy-01

EXPNO 10

PROCNO 1

Date_ 20160628

Time 14.52

INSTRUM spect


PULPROG zg30

TD 65536

SOLVENT CDCl3

NS 16

DS 0

SWH 8223.685 Hz

FIDRES 0.125483 Hz

AQ 3.9846387 sec

RG 203

DW 60.800 usec

DE 6.50 usec

TE 295.3 K

D1 1.00000000 sec

TD0 1

======== CHANNEL f1 ========

NUC1 1H

P1 14.75 usec

PL1 -1.00 dB

PL1W 13.37643433 W

SFO1 400.1324710 MHz

SI 32768

SF 400.1300078 MHz

WDW EM

SSB 0

LB 0.30 Hz

GB 0

PC 1.00

13C NMR (CDCl3, 100 MHz) spectrum of compound 4a:

-100102030405060708090100110120130140150160170180190200210

f1 (ppm)

35.24

40.89

41.06

100.87

108.30

109.03

121.61

125.12

128.37

130.41

132.44

133.33

133.57

146.11

147.72

148.80

168.93

NAME sx-qhy-08EXPNO 10PROCNO 1Date_ 20160712Time 22.32INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zgpg30TD 65536SOLVENT CDCl3NS 400DS 0SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 203DW 20.800 usecDE 6.50 usecTE 297.1 KD1 2.00000000 secD11 0.03000000 secTD0 1



NH

O

OO

O2N

4a

NH

O

OO

O2N

4a

S9

1H NMR (DMSO-d6, 400 MHz) spectrum of compound 4b:

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5

f1 (ppm)2.02

2.06

1.92

6.17

2.17

1.00

1.99

1.03

1.04

1.00

1038.19

1045.42

1052.69

1276.95

1282.85

1284.58

1288.85

1290.40

1297.12

1527.93

1541.25

1546.67

2375.16

2384.71

2390.30

2392.08

2656.18

2657.92

2664.08

2665.82

2668.99

2714.74

2716.37

2719.56

2723.42

2727.45

2819.33

3052.37

3057.43

3185.08

3190.69

3196.29

NAME sx-qhy-38

EXPNO 10

PROCNO 1

Date_ 20170515

Time 14.33

INSTRUM spect


PULPROG zg30

TD 65536

SOLVENT DMSO

NS 16

DS 0

SWH 8223.685 Hz

FIDRES 0.125483 Hz

AQ 3.9846387 sec

RG 203

DW 60.800 usec

DE 6.50 usec

TE 297.2 K

D1 1.00000000 sec

TD0 1

======== CHANNEL f1 ========

NUC1 1H

P1 14.75 usec

PL1 -1.00 dB

PL1W 13.37643433 W

SFO1 400.1324710 MHz

SI 32768

SF 400.1300010 MHz

WDW EM

SSB 0

LB 0.30 Hz

GB 0

PC 1.00

13C NMR (DMSO-d6, 100 MHz) spectrum of compound 4b:

-100102030405060708090100110120130140150160170180190200210

f1 (ppm)

34.84

40.00

55.90

56.10

100.58

107.94

108.02

108.98

115.36

121.43

126.01

133.25

140.92

145.42

147.10

147.16

152.57

168.62

NAME sx-qhy-38EXPNO 10PROCNO 1Date_ 20170519Time 2.58INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zgpg30TD 65536SOLVENT DMSONS 400DS 0SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 203DW 20.800 usecDE 6.50 usecTE 296.4 KD1 2.00000000 secD11 0.03000000 secTD0 1



NH

O

O O

4b

O2N

MeO OMe

NH

O

O O

4b

O2N

MeO OMe

S10

1H NMR (DMSO-d6, 400 MHz) spectrum of compound 4c:

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0

f1 (ppm)2.07

2.08

2.02

2.13

2.11

1.03

2.08

1.02

0.95

1.00

1038.29

1045.49

1052.76

1278.31

1285.09

1291.77

1298.53

1310.74

1506.38

2385.83

2398.18

2471.86

2488.77

2510.26

2656.64

2658.29

2664.53

2666.21

2701.02

2716.40

2717.88

2720.12

2728.25

2738.07

2804.63

3051.85

3203.13

3208.83

3214.51

NAME sx-quy-26

EXPNO 10

PROCNO 1

Date_ 20170105

Time 22.03

INSTRUM spect


PULPROG zg30

TD 65536

SOLVENT DMSO

NS 16

DS 0

SWH 8223.685 Hz

FIDRES 0.125483 Hz

AQ 3.9846387 sec

RG 90.5

DW 60.800 usec

DE 6.50 usec

TE 294.2 K

D1 1.00000000 sec

TD0 1

======== CHANNEL f1 ========

NUC1 1H

P1 14.75 usec

PL1 -1.00 dB

PL1W 13.37643433 W

SFO1 400.1324710 MHz

SI 32768

SF 400.1299997 MHz

WDW EM

SSB 0

LB 0.30 Hz

GB 0

PC 1.00

13C NMR (DMSO-d6, 100 MHz) spectrum of compound 4c:

-100102030405060708090100110120130140150160170180190200210

f1 (ppm)

34.82

39.95

40.61

100.58

103.20

105.08

108.03

108.99

111.87

121.45

128.10

133.20

142.63

145.43

146.53

147.11

151.26

168.40

NAME sx-quy-26EXPNO 11PROCNO 1Date_ 20170105Time 22.27INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zgpg30TD 65536SOLVENT DMSONS 400DS 0SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 203DW 20.800 usecDE 6.50 usecTE 294.9 KD1 2.00000000 secD11 0.03000000 secTD0 1



O

O NHO

4c

O2N

O O

O

O NHO

4c

O2N

O O

S11

1H NMR (CDCl3, 400 MHz) spectrum of compound 4d:

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)

2.11

2.11

2.05

3.03

3.00

2.05

1.05

2.07

1.04

1.00

1084

.71

1091

.67

1098

.62

1385

.09

1392

.03

1396

.87

1398

.93

1510

.67

1535

.11

1538

.26

2659

.22

2661

.03

2667

.36

2669

.10

2673

.15

2674

.85

2697

.38

2705

.42

2967

.43

2973

.50

2975

.09

3030

.03

3198

.67

3199

.46

3206

.87

3208

.25 NAME sx-lx-201



PC 1.00

13C NMR (CDCl3, 100 MHz) spectrum of compound 4d:

-100102030405060708090100110120130140150160170180190200210f1 (ppm)

35.1

040

.85

40.9

4

55.8

455

.92

111.

3211

1.90

120.

6012

5.12

128.

3913

0.38

131.

2013

3.37

133.

58

147.

6214

8.76

148.

98

168.

88

NAME sx-lx-2020EXPNO 10PROCNO 1Date_ 20160322Time 0.49INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zgpg30TD 65536SOLVENT CDCl3NS 400DS 0SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 203DW 20.800 usecDE 6.50 usecTE 296.4 KD1 2.00000000 secD11 0.03000000 secTD0 1


======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL2 -1.00 dBPL12 14.71 dBPL13 17.90 dBPL2W 13.37643433 WPL12W 0.35920334 WPL13W 0.17232187 WSFO2 400.1316005 MHzSI 32768SF 100.6127690 MHzWDW EMSSB 0LB 1.00 HzGB 0

PC 1.40

NH

MeO

MeO OO2N

4d

NH

MeO

MeO OO2N

4d

S12

1H NMR (CDCl3, 400 MHz) spectrum of compound 4e:

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)

2.05

2.09

2.02

3.00

3.07

3.08

2.99

1.00

2.02

1.04

1.00

1.00

1084

.67

1091

.54

1098

.34

1384

.85

1391

.34

1397

.34

1403

.90

1507

.72

1534

.04

1538

.81

1577

.21

1583

.96

2382

.62

2654

.93

2663

.11

2666

.01

2691

.76

2699

.75

2732

.85

3041

.95 NAME sx-lx-101



PC 1.00

13C NMR (CDCl3, 100 MHz) spectrum of compound 4e:

-100102030405060708090100110120130140150160170180190200210f1 (ppm)

35.0

940

.90

41.3

9

55.8

255

.87

56.3

556

.57

108.

1511

1.23

111.

8811

4.44

120.

5612

5.48

131.

14

140.

80

147.

5914

8.07

148.

9615

3.35 NAME sx-lx-1010




NH

MeO

MeO O

4e

O2N

MeO OMe

NH

MeO

MeO O

4e

O2N

MeO OMe

S13

1H NMR (CDCl3, 400 MHz) spectrum of compound 4f:

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)

2.02

2.05

2.11

9.03

0.96

1.00

1.00

2.02

1.04

1.00

1093

.90

1373

.63

1377

.40

1521

.41

1536

.23

1540

.94

2483

.20

2627

.92

2636

.13

2707

.06

2715

.24

2976

.82

3025

.89

3032

.68

3206

.81

3214

.74

NAME sx-zb-910EXPNO 10PROCNO 1Date_ 20150825Time 15.52INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 0SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 71.8DW 60.800 usecDE 6.50 usecTE 2955.0 KD1 1.00000000 secTD0 1


13C NMR (CDCl3, 100 MHz) spectrum of compound 4f:

0102030405060708090100110120130140150160170180190200f1 (ppm)

29.6

3

40.9

4

56.0

060

.74

60.9

8

107.

43

124.

5112

4.74

125.

0612

8.28

130.

5313

3.42

133.

4914

2.19

148.

8915

1.80

152.

58

168.

94 NAME sx-zb-910EXPNO 10PROCNO 1Date_ 20150825Time 16.16INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zgpg30TD 65536SOLVENT CDCl3NS 400DS 0SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 203DW 20.800 usecDE 6.50 usecTE 2962.0 KD1 2.00000000 secD11 0.03000000 secTD0 1



NH

OMeMeO

MeOO2N

4f

O

NH

OMeMeO

MeOO2N

4f

O

S14

1H NMR (CDCl3-TFA, 400 MHz) spectrum of compound 6a:

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0

f1 (ppm)

2.00

1.00

2.07

1.07

1.01

1.00

1.02

1.00

2556.01

2561.83

2959.77

3138.80

3140.31

3146.20

3147.84

3150.08

3156.57

3158.12

3164.44

3165.92

3183.02

3184.23

3190.50

3191.75

3198.08

3199.25

3234.26

3240.50

3272.99

3279.34

3315.86

3316.99

3324.12

3325.25

3368.36

NAME sx-qhy-35

EXPNO 10

PROCNO 1

Date_ 20170510

Time 14.48

INSTRUM spect


PULPROG zg30

TD 65536

SOLVENT CDCl3-TFA

NS 16

DS 0

SWH 8223.685 Hz

FIDRES 0.125483 Hz

AQ 3.9846387 sec

RG 203

DW 60.800 usec

DE 6.50 usec

TE 295.7 K

D1 1.00000000 sec

TD0 1

======== CHANNEL f1 ========

NUC1 1H

P1 14.75 usec

PL1 -1.00 dB

PL1W 13.37643433 W

SFO1 400.1324710 MHz

SI 32768

SF 400.1300084 MHz

WDW EM

SSB 0

LB 0.30 Hz

GB 0

PC 1.00


-100102030405060708090100110120130140150160170180190200210

f1 (ppm)

103.16

103.78

104.36

124.52

125.39

126.47

130.20

131.08

131.80

134.04

135.87

141.68

142.08

146.24

154.17

156.93

186.14

NAME sx-qhy-35EXPNO 10PROCNO 1Date_ 20170505Time 0.55INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zgpg30TD 65536SOLVENT CDCl3+TFANS 400DS 0SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 203DW 20.800 usecDE 6.50 usecTE 296.3 KD1 2.00000000 secD11 0.03000000 secTD0 1



N

O

O

OO2N

6a

N

O

O

OO2N

6a

S15

1H NMR (CDCl3-TFA, 400 MHz) spectrum of compound 6b:

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.511.0

f1 (ppm)

2.00

0.84

1.01

1.01

1.00

0.99

1.00

1611.08

1620.76

1625.91

1636.88

2548.27

2558.13

2906.65

2952.18

3081.99

3220.25

3226.42

3259.36

3265.70

3349.70

NAME sx-qhy-40

EXPNO 10

PROCNO 1

Date_ 20170518

Time 16.07

INSTRUM spect


PULPROG zg30

TD 65536

SOLVENT CDCl3-TFA

NS 16

DS 0

SWH 8223.685 Hz

FIDRES 0.125483 Hz

AQ 3.9846387 sec

RG 203

DW 60.800 usec

DE 6.50 usec

TE 295.7 K

D1 1.00000000 sec

TD0 1

======== CHANNEL f1 ========

NUC1 1H

P1 14.75 usec

PL1 -1.00 dB

PL1W 13.37643433 W

SFO1 400.1324710 MHz

SI 32768

SF 400.1300079 MHz

WDW EM

SSB 0

LB 0.30 Hz

GB 0

PC 1.00

13C NMR (CDCl3-TFA, 100 MHz) spectrum of compound 6b:

-100102030405060708090100110120130140150160170180190200210

f1 (ppm)

56.73

56.88

103.35

103.81

103.84

107.34

112.93

124.55

125.71

126.75

131.12

139.96

140.54

144.56

152.19

153.24

154.82

155.78

187.14

NAME sx-quy-40EXPNO 10PROCNO 1Date_ 20170525Time 23.42INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zgpg30TD 65536SOLVENT CDCl3+TFANS 400DS 0SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 203DW 20.800 usecDE 6.50 usecTE 297.4 KD1 2.00000000 secD11 0.03000000 secTD0 1



N

O

O

O

6b

O2N

MeO OMe

N

O

O

O

6b

O2N

MeO OMe

S16

1H NMR (CDCl3-TFA, 400 MHz) spectrum of compound 6c:

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.511.0

f1 (ppm)

2.04

2.03

1.02

0.99

1.01

1.02

1.02

1.00

2510.81

2518.38

2555.19

2560.30

2862.76

2866.55

2871.07

2951.90

3051.90

3055.43

3226.17

3232.47

3279.48

3285.80

3352.53

NAME sx-qhy-39

EXPNO 10

PROCNO 1

Date_ 20170515

Time 14.39

INSTRUM spect


PULPROG zg30

TD 65536

SOLVENT CDCl3-TFA

NS 16

DS 0

SWH 8223.685 Hz

FIDRES 0.125483 Hz

AQ 3.9846387 sec

RG 203

DW 60.800 usec

DE 6.50 usec

TE 296.8 K

D1 1.00000000 sec

TD0 1

======== CHANNEL f1 ========

NUC1 1H

P1 14.75 usec

PL1 -1.00 dB

PL1W 13.37643433 W

SFO1 400.1324710 MHz

SI 32768

SF 400.1300081 MHz

WDW EM

SSB 0

LB 0.30 Hz

GB 0

PC 1.00

13C NMR (CDCl3-TFA, 100 MHz) spectrum of compound 6c:

-100102030405060708090100110120130140150160170180190200210

f1 (ppm)

103.62

103.62

104.22

104.87

105.43

109.97

124.54

126.18

128.24

130.04

141.62

141.76

142.54

151.96

153.93

154.12

156.70

185.29




O

O N

O

6c

O2N

O O

O

O N

O

6c

O2N

O O

S17


0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)

3.11

3.06

1.03

2.07

1.01

1.05

1.00

1.01

1.00

1619

.26

1656

.82

2839

.85

3042

.79

3048

.13

3082

.18

3120

.51

3121

.52

3253

.55

3254

.35

3291

.83

3297

.18

3498

.71 NAME sx-lx-202



PC 1.00


-100102030405060708090100110120130140150160170180190200210f1 (ppm)

56.0

756

.26

104.

5310

4.74

123.

5512

3.66

123.

6712

9.66

130.

2913

4.02

134.

5413

7.94

140.

1514

7.59

148.

3515

2.47

153.

08

195.

63

NAME sx-lx-2020EXPNO 11PROCNO 1Date_ 20160319Time 10.32INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zgpg30TD 65536SOLVENT CDCl3NS 400DS 0SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 203DW 20.800 usecDE 6.50 usecTE 297.0 KD1 2.00000000 secD11 0.03000000 secTD0 1



N

MeO

MeO

O

6d

O2N

N

MeO

MeO

O

6d

O2N

S18


0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)

5.68

3.13

3.03

1.00

1.00

0.80

1.06

0.91

1.00

1606

.04

1615

.87

1651

.19

2834

.82

2847

.89

3044

.14

3058

.83

3294

.99

3459

.53 NAME sx-lx-102



PC 1.00


-100102030405060708090100110120130140150160170180190200210f1 (ppm)

56.0

756

.22

56.5

756

.64

104.

6110

4.72

106.

4611

1.05

123.

54

132.

0513

4.44

140.

0114

0.57

149.

0614

9.68

152.

3015

3.06

153.

69

195.

33 NAME sx-lx-1020EXPNO 10PROCNO 1Date_ 20160404Time 18.39INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zgpg30TD 65536SOLVENT CDCl3NS 400DS 0SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 203DW 20.800 usecDE 6.50 usecTE 295.7 KD1 2.00000000 secD11 0.03000000 secTD0 1



PC 1.40

N

MeO

MeO

O

6e

O2N

MeO OMe

N

MeO

MeO

O

6e

O2N

MeO OMe

S19


0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)

6.04

3.08

2.01

1.02

1.01

0.99

1.00

1.00

1621

.27

1648

.16

3053

.30

3060

.85

3068

.73

3075

.64

3083

.02

3114

.56

3121

.89

3129

.15

3198

.93

3204

.04

3255

.02

3263

.10

3301

.77

3306

.95

3424

.42




0102030405060708090100110120130140150160170180190200f1 (ppm)

56.2

661

.23

61.7

0

100.

86

119.

1312

3.58

124.

4512

9.69

129.

8413

0.33

134.

0713

7.92

139.

5514

4.13

146.

5114

7.48

148.

6315

6.02

195.

45

NAME sx-zy-911EXPNO 10PROCNO 1Date_ 20150825Time 16.45INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zgpg30TD 65536SOLVENT CDCl3NS 400DS 0SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 203DW 20.800 usecDE 6.50 usecTE 2962.0 KD1 2.00000000 secD11 0.03000000 secTD0 1



N

MeO

MeO

6f

OMe

OO2N

N

MeO

MeO

6f

OMe

OO2N

S20

1H NMR (CDCl3, 400 MHz) spectrum of compound 6g:

13C NMR (CDCl3, 100 MHz) spectrum of compound 6g:

N

O

MeO

MeO

6g

MeO

N

O

MeO

MeO

6g

MeO

S21

1H NMR (CDCl3, 400 MHz) spectrum of compound 6h:

13C NMR (CDCl3, 100 MHz) spectrum of compound 6h:

N

O

MeO

MeO

MeO

6h

N

O

MeO

MeO

MeO

6h

S22

1H NMR (CDCl3, 400 MHz) spectrum of compound 6i:

13C NMR (CDCl3, 100 MHz) spectrum of compound 6i:

N

O

MeO

MeO

MeO

6i

MeO

N

O

MeO

MeO

MeO

6i

MeO

S23

1H NMR (CDCl3, 400 MHz) spectrum of compound 6j:

13C NMR (CDCl3, 100 MHz) spectrum of compound 6j:

N

O

MeO

MeO

6j

N

O

MeO

MeO

6j

S24

1H NMR (CDCl3, 400 MHz) spectrum of compound 6k:

13C NMR (CDCl3, 100 MHz) spectrum of compound 6k:

N

O

MeO

6k

MeO

N

O

MeO

6k

MeO

S25

1H NMR (CDCl3, 400 MHz) spectrum of compound 6l:

13C NMR (CDCl3, 100 MHz) spectrum of compound 6l:

N

O

MeO

MeO

6l

N

O

MeO

MeO

6l

S26

1H NMR (CDCl3, 400 MHz) spectrum of compound 6m:

13C NMR (CDCl3, 100 MHz) spectrum of compound 6m:

N

O

MeO

MeO6m

MeO

N

O

MeO

MeO6m

MeO

S27

1H NMR (CDCl3, 400 MHz) spectrum of compound 6n:

13C NMR (CDCl3, 100 MHz) spectrum of compound 6n:

N

O

MeO

6n

N

O

MeO

6n

S28

1H NMR (CDCl3, 400 MHz) spectrum of compound 6o:

13C NMR (CDCl3, 100 MHz) spectrum of compound 6o:

N

O

6o

MeO

N

O

6o

MeO

S29

1H NMR (CDCl3, 400 MHz) spectrum of compound 6p:

13C NMR (CDCl3, 100 MHz) spectrum of compound 6p:

N

O

MeO6p

N

O

MeO6p

S30

1H NMR (CDCl3, 400 MHz) spectrum of compound 6q:

13C NMR (CDCl3, 100 MHz) spectrum of compound 6q:

N

O

MeO6q

MeO

N

O

MeO6q

MeO

S31

1H NMR (CDCl3, 400 MHz) spectrum of compound 6r:

13C NMR (CDCl3, 100 MHz) spectrum of compound 6r:

N

O

6r

N

O

6r

S32

1H NMR (CDCl3, 400 MHz) spectrum of compound 6s:

13C NMR (CDCl3, 100 MHz) spectrum of compound 6s:

N

O

Br

O

O

6s

N

O

Br

O

O

6s

S33

1H NMR (CDCl3, 400 MHz) spectrum of compound 6t:

13C NMR (CDCl3, 100 MHz) spectrum of compound 6t:

N

O

OMeMeO

MeO

MeO 6t

N

O

OMeMeO

MeO

MeO 6t

S34

1H NMR (DMSO-d6, 400 MHz) spectrum of compound 7a:

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0

f1 (ppm)

2.00

1.03

2.05

0.98

1.07

1.04

1.93

1.01

1.00

2486.54

2503.53

2540.92

2542.09

2547.81

2548.95

2550.21

2556.03

2557.12

2754.80

2755.85

2757.41

2759.13

2763.22

2764.39

2765.62

2767.16

2811.97

2894.45

2903.89

2908.46

2910.02

2915.35

2916.98

2918.53

2923.80

2925.40

2988.52

3025.46

3110.58

3111.36

3116.23

3117.03

3341.51

3346.85

3352.40

NAME sx-quy-11

EXPNO 10

PROCNO 1

Date_ 20160713

Time 12.36

INSTRUM spect


PULPROG zg30

TD 65536

SOLVENT DMSO

NS 16

DS 0

SWH 8223.685 Hz

FIDRES 0.125483 Hz

AQ 3.9846387 sec

RG 203

DW 60.800 usec

DE 6.50 usec

TE 295.9 K

D1 1.00000000 sec

TD0 1

======== CHANNEL f1 ========

NUC1 1H

P1 14.75 usec

PL1 -1.00 dB

PL1W 13.37643433 W

SFO1 400.1324710 MHz

SI 32768

SF 400.1299982 MHz

WDW EM

SSB 0

LB 0.30 Hz

GB 0

PC 1.00

13C NMR (DMSO-d6, 100 MHz) spectrum of compound 7a:

-100102030405060708090100110120130140150160170180190200210

f1 (ppm)

100.59

102.21

102.77

114.16

115.83

116.90

120.89

122.04

134.12

134.73

135.06

140.43

148.81

150.85

152.65

156.03

196.49




N

O

O

OH2N

7a

N

O

O

OH2N

7a

S35

1H NMR (DMSO-d6, 400 MHz) spectrum of compound 7b:

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0

f1 (ppm)

3.23

3.11

2.09

1.02

1.01

1.01

1.06

2.06

1.05

1.00

1373.31

1381.39

1390.23

1507.79

1521.48

2478.02

2560.26

2592.40

2821.42

2963.60

3026.21

3092.28

3097.87

3344.96

3350.50

NAME sx-quy-21

EXPNO 10

PROCNO 1

Date_ 20170523

Time 18.33

INSTRUM spect


PULPROG zg30

TD 65536

SOLVENT DMSO

NS 16

DS 0

SWH 8223.685 Hz

FIDRES 0.125483 Hz

AQ 3.9846387 sec

RG 57

DW 60.800 usec

DE 6.50 usec

TE 296.2 K

D1 1.00000000 sec

TD0 1

======== CHANNEL f1 ========

NUC1 1H

P1 14.75 usec

PL1 -1.00 dB

PL1W 13.37643433 W

SFO1 400.1324710 MHz

SI 32768

SF 400.1300000 MHz

WDW EM

SSB 0

LB 0.30 Hz

GB 0

PC 1.00

13C NMR (DMSO-d6, 100 MHz) spectrum of compound 7b:

-100102030405060708090100110120130140150160170180190200210

f1 (ppm)

55.41

56.07

98.61

100.79

102.17

102.75

108.04

115.72

120.74

122.05

134.74

138.72

140.36

148.67

150.76

150.85

156.34

156.42

193.52

NAME sx-qmy-22EXPNO 10PROCNO 1Date_ 20161101Time 21.40INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zgpg30TD 65536SOLVENT DMSONS 400DS 0SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 203DW 20.800 usecDE 6.50 usecTE 295.4 KD1 2.00000000 secD11 0.03000000 secTD0 1



N

O

O

O

7b

H2N

MeO OMe

N

O

O

O

7b

H2N

MeO OMe

S36

1H NMR (DMSO-d6, 400 MHz) spectrum of compound 7c:

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0

f1 (ppm)

1.96

1.04

1.75

1.00

0.95

0.98

1.08

1.74

1.00

2362.29

2476.49

2480.18

2485.37

2585.46

2806.38

2977.89

3098.37

3103.96

3134.46

3340.41

3345.95

3349.55

3351.15

NAME sx-qhy-28

EXPNO 10

PROCNO 1

Date_ 20170221

Time 21.04

INSTRUM spect


PULPROG zg30

TD 65536

SOLVENT DMSO

NS 16

DS 0

SWH 8223.685 Hz

FIDRES 0.125483 Hz

AQ 3.9846387 sec

RG 114

DW 60.800 usec

DE 6.50 usec

TE 377.0 K

D1 1.00000000 sec

TD0 1

======== CHANNEL f1 ========

NUC1 1H

P1 14.75 usec

PL1 -1.00 dB

PL1W 13.37643433 W

SFO1 400.1324710 MHz

SI 32768

SF 400.1299957 MHz

WDW EM

SSB 0

LB 0.30 Hz

GB 0

PC 1.00

13C NMR (DMSO-d6, 100 MHz) spectrum of compound 7c:

-100102030405060708090100110120130140150160170180190200210

f1 (ppm)

95.69

100.70

101.29

102.17

102.75

108.08

109.29

120.70

121.90

134.70

137.27

140.41

148.66

150.77

152.51

153.63

156.33

193.22




O

O N

O

7c

H2N

O O

O

O N

O

7c

H2N

O O

S37


0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)

3.00

3.14

1.10

2.04

1.21

1.02

2.17

1.05

1.03

1549

.62

1595

.32

2577

.20

2577

.82

2585

.06

2592

.31

2592

.91

2640

.95

2674

.89

2683

.15

2841

.01

2877

.27

2884

.32

3023

.87

3029

.44

3363

.80

3369

.35 NAME sx-lx-203

EXPNO 10PROCNO 1Date_ 20160330Time 12.56INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 0SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 40.3DW 60.800 usecDE 6.50 usecTE 295.0 KD1 1.00000000 secTD0 1


PC 1.00


0102030405060708090100110120130140150160170180190200210f1 (ppm)

56.0

456

.10

103.

9410

4.95

115.

5711

7.06

117.

4612

0.45

122.

06

133.

7713

4.79

135.

2014

0.34

150.

7215

2.11

153.

1415

5.57

197.




N

MeO

MeO

O

7d

H2N

N

MeO

MeO

O

7d

H2N

S38


0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)

3.09

2.98

3.07

3.08

1.04

1.93

1.04

1.01

1.05

1.02

1.00

1400

.60

1556

.47

1571

.35

1617

.68

2478

.81

2623

.41

2672

.82

2850

.24

2930

.91

3032

.12

3037

.64

3371

.41

3376

.96 NAME sx-lx-103




-100102030405060708090100110120130140150160170180190200210f1 (ppm)

55.9

356

.10

56.1

256

.38

98.8

210

4.21

104.

8810

9.84

115.

9712

0.34

122.

09

133.

8614

0.01

140.

32

149.

9615

0.65

153.

1415

5.80

156.

42

195.




N

MeO

MeO

O

7e

H2N

MeO OMe

N

MeO

MeO

O

7e

H2N

MeO OMe

S39


0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)

2.98

3.00

3.00

2.67

1.08

1.01

0.99

1.14

1.00

1.00

1554

.73

1607

.82

1630

.05

2592

.13

2599

.47

2607

.21

2690

.29

2698

.63

2840

.00

2878

.06

2886

.15

2909

.85

3175

.88

3181

.53

3385

.25

3390

.93




0102030405060708090100110120130140150160170180190200f1 (ppm)

56.1

061

.23

61.6

2

100.

23

115.

6811

5.73

117.

0411

7.47

123.

1412

9.00

134.

8713

5.27

139.

8214

4.28

146.

7915

2.04

154.

3015

5.80

197.

48 NAME sx-zb-912EXPNO 11PROCNO 1Date_ 20150829Time 5.54INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zgpg30TD 65536SOLVENT CDCl3NS 400DS 0SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 203DW 20.800 usecDE 6.50 usecTE 2962.0 KD1 2.00000000 secD11 0.03000000 secTD0 1



N

MeO

MeO

7f

OMe

OH2N

N

MeO

MeO

7f

OMe

OH2N

S40

1H NMR (CDCl3-TFA, 400 MHz) spectrum of compound 1a:

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0

f1 (ppm)

1.96

0.99

1.00

1.00

0.94

0.98

1.05

1.00

2652.06

2990.67

3060.32

3061.22

3068.41

3076.00

3162.78

3164.16

3170.76

3172.08

3178.26

3179.66

3341.64

3347.48

3366.96

3368.35

3374.91

3376.34

3449.86

3461.83

3469.90

3507.44

3513.44

NAME sx-quy-36

EXPNO 10

PROCNO 1

Date_ 20170509

Time 16.32

INSTRUM spect


PULPROG zg30

TD 65536

SOLVENT CDCl3-TFA

NS 16

DS 0

SWH 8223.685 Hz

FIDRES 0.125483 Hz

AQ 3.9846387 sec

RG 203

DW 60.800 usec

DE 6.50 usec

TE 295.5 K

D1 1.00000000 sec

TD0 1

======== CHANNEL f1 ========

NUC1 1H

P1 14.75 usec

PL1 -1.00 dB

PL1W 13.37643433 W

SFO1 400.1324710 MHz

SI 32768

SF 400.1300081 MHz

WDW EM

SSB 0

LB 0.30 Hz

GB 0

PC 1.00


-100102030405060708090100110120130140150160170180190200210

f1 (ppm)

103.66

105.20

108.14

122.36

126.79

128.08

128.27

129.11

130.37

132.15

133.94

134.99

137.16

143.26

152.03

158.50

176.51




N

O

O

O

Liriodenine 1a

N

O

O

O

Liriodenine 1a

S41

1H NMR (CDCl3-TFA, 400 MHz) spectrum of compound 1b:

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5

f1 (ppm)

3.08

2.99

2.02

1.02

1.03

1.03

1.00

1.00

1615.67

1642.12

2652.31

2973.81

3128.18

3220.96

3329.72

3335.23

3494.44

3500.17

NAME sx-qhy-34

EXPNO 10

PROCNO 1

Date_ 20170329

Time 17.12

INSTRUM spect


PULPROG zg30

TD 65536

SOLVENT CDCl3-TFA

NS 16

DS 0

SWH 8223.685 Hz

FIDRES 0.125483 Hz

AQ 3.9846387 sec

RG 203

DW 60.800

usec

DE 6.50

usec

TE 295.3 K

D1 1.00000000 sec

TD0 1

======== CHANNEL f1

========

NUC1 1H

P1 14.75

usec

PL1 -1.00 dB

PL1W 13.37643433 W

SFO1 400.1324710 MHz

SI 32768

SF 400.1300065 MHz

WDW EM

SSB 0

LB 0.30 Hz

GB 0

PC 1.00

13C NMR (CDCl3-TFA, 100 MHz) spectrum of compound 1b:

-100102030405060708090100110120130140150160170180190200210

f1 (ppm)

56.16

56.46

103.58

105.40

108.06

109.64

109.71

121.78

122.59

126.63

129.04

133.57

135.07

143.27

150.56

152.03

157.13

158.63

174.96




N

O

O

O

OMeMeO

Dicentrinone 1b

N

O

O

O

OMeMeO

Dicentrinone 1b

S42

1H NMR (CDCl3-TFA, 400 MHz) spectrum of compound 1c:

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5

f1 (ppm)

1.95

1.92

0.98

0.97

0.98

0.99

1.00

2485.99

2493.33

2502.75

2639.13

2646.34

2981.58

3104.57

3107.78

3242.06

3245.29

3337.48

3343.71

3484.43

3490.68

NAME sx-qhy-33

EXPNO 10

PROCNO 1

Date_ 20170321

Time 13.40

INSTRUM spect


PULPROG zg30

TD 65536

SOLVENT CDCl3-TFA

NS 16

DS 0

SWH 8223.685 Hz

FIDRES 0.125483 Hz

AQ 3.9846387 sec

RG 90.5

DW 60.800 usec

DE 6.50 usec

TE 293.6 K

D1 1.00000000 sec

TD0 1

======== CHANNEL f1 ========

NUC1 1H

P1 14.75 usec

PL1 -1.00 dB

PL1W 13.37643433 W

SFO1 400.1324710 MHz

SI 32768

SF 400.1300071 MHz

WDW EM

SSB 0

LB 0.30 Hz

GB 0

PC 1.00

13C NMR (CDCl3-TFA, 100 MHz) spectrum of compound 1c:

-100102030405060708090100110120130140150160170180190200210

f1 (ppm)

103.54

103.55

105.34

107.12

107.52

108.03

121.60

124.25

126.58

130.79

133.71

134.79

143.18

150.01

152.30

156.46

158.64

174.76




Cassameridine 1c

N

O

O

O

OO

Cassameridine 1c

N

O

O

O

OO

S43


0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)

3.00

3.00

1.00

1.01

2.02

1.01

1.00

1.00

1608

.03

1640

.42

2888

.08

3100

.15

3101

.65

3108

.72

3109

.81

3115

.88

3121

.20

3430

.78

3432

.03

3438

.62

3439

.84

3556

.69

3561

.89

3665

.77

3674

.09 NAME sx-lx-204



PC 1.00


-100102030405060708090100110120130140150160170180190200210f1 (ppm)

56.2

3

60.6

7

106.

48

119.

8412

2.11

123.

5812

8.45

128.

8012

8.90

132.

1113

4.34

135.

5014

5.05

145.

39

152.

0515

2.08

156.

85

182.

71

NAME sx-zy-34

EXPNO 10

PROCNO 1

Date_ 20160401

Time 5.27

INSTRUM spect


PULPROG zgpg30

TD 65536

SOLVENT CDCl3

NS 400

DS 0

SWH 24038.461 Hz

FIDRES 0.366798 Hz

AQ 1.3631988 sec

RG 203

DW 20.800 usec

DE 6.50 usec

TE 295.8 K

D1 2.00000000 sec

D11 0.03000000 sec

TD0 1

======== CHANNEL f1 ========

NUC1 13C

P1 9.85 usec

PL1 -2.20 dB

PL1W 60.02919006 W

SFO1 100.6228298 MHz

======== CHANNEL f2 ========

CPDPRG2 waltz16

NUC2 1H

PCPD2 90.00 usec

PL2 -1.00 dB

PL12 14.71 dB

PL13 17.90 dB

PL2W 13.37643433 W

PL12W 0.35920334 W

PL13W 0.17232187 W

SFO2 400.1316005 MHz

SI 32768

SF 100.6127690 MHz

WDW EM

SSB 0

LB 1.00 Hz

GB 0

PC 1.40

N

MeO

MeO

O

Lysicamine 1d

N

MeO

MeO

O

Lysicamine 1d

S44


0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)

3.17

5.93

3.22

1.03

1.04

1.00

1.00

1.00

1594

.75

1614

.83

1616

.03

1623

.38

2845

.24

3075

.01

3080

.20

3179

.77

3488

.34

3526

.33

3531

.49 NAME sx-lx-104



PC 1.00


-100102030405060708090100110120130140150160170180190200210f1 (ppm)

55.9

856

.18

60.5

7

105.

9810

9.67

110.

13

119.

7312

1.53

123.

3012

6.76

129.

0513

5.25

144.

8114

5.38

149.

3915

0.91

153.

6515

6.60

181.




PC 1.40

N

MeO

MeO

OMeMeO

O

Oxoglaucine 1e

N

MeO

MeO

OMeMeO

O

Oxoglaucine 1e

S45


0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0

f1 (ppm)

3.00

3.07

3.04

1.06

1.07

0.98

1.00

1.00

1.02

1598

.84

1610

.62

1645

.06

2963

.46

2970

.96

2978

.37

3048

.51

3056

.66

3063

.92

3242

.02

3246

.24

3381

.82

3389

.54

3542

.55

3546

.51

3595

.46

3603

.81

Current Data ParametersNAME 150825-SX-ZB-913EXPNO 1PROCNO 1

F2 - Acquisition ParametersDate_ 20150825Time 20.42INSTRUM spectPROBHD 5 mm PABBO BB/PULPROG zg30TD 65536SOLVENT CDCl3NS 8DS 2SWH 8012.820 HzFIDRES 0.122266 HzAQ 4.0894465 secRG 45.2DW 62.400 usecDE 6.50 usecTE 292.1 KD1 1.00000000 secTD0 1

======== CHANNEL f1 ========SFO1 400.1324710 MHzNUC1 1HP1 13.70 usecPLW1 9.17000008 W

F2 - Processing parametersSI 65536SF 400.1300343 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00


102030405060708090100110120130140150160170180190200f1 (ppm)

60.9

961

.46

61.8

1

115.

5611

9.12

122.

7712

7.64

128.

0812

8.85

131.

0113

1.38

134.

3413

4.51

144.

5214

5.43

147.

2514

8.45

156.

48

182.

59 Current Data ParametersNAME 150825-SX-ZB-913EXPNO 2PROCNO 1

F2 - Acquisition ParametersDate_ 20150825Time 21.41INSTRUM spectPROBHD 5 mm PABBO BB/PULPROG zgpg30TD 65536SOLVENT CDCl3NS 1024DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631488 secRG 203DW 20.800 usecDE 6.50 usecTE 292.7 KD1 2.00000000 secD11 0.03000000 secTD0 1

======== CHANNEL f1 ========SFO1 100.6228293 MHzNUC1 13CP1 9.00 usecPLW1 56.42200089 W

======== CHANNEL f2 ========SFO2 400.1316005 MHzNUC2 1HCPDPRG[2 waltz16PCPD2 90.00 usecPLW2 9.17000008 WPLW12 0.21247999 WPLW13 0.17211001 W

F2 - Processing parametersSI 32768SF 100.6127690 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40

N

O

OMeMeO

MeO

O-Methylmoschatoline 1f

N

O

OMeMeO

MeO

O-Methylmoschatoline 1f

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