Journal of Synthetic organic Chemistry SUPPORTING INFORMATIONSYNTHESIS

Thieme

Supporting Information for DOI: 10.1055/s-0030-1260073

© Georg Thieme Verlag KG Stuttgart · New York 2011

1

Electronic Supporting Information

One-pot synthesis of fused tetracyclic scaffolds via Lewis acid-catalyzed tandem reaction of naphthoquinones

Yassine Bendiabdellah, Isabel Villanueva-Margalef, Antonio Misale, Kazi S. Nahar, Mohammad R. Haque, David E. Thurston and Giovanna Zinzalla*

CRUK Protein-Protein interactions Drug Discovery Research Group

Department of Biological and Pharmaceutical Chemistry, School of Pharmacy, University of London, 29-39 Brunswick Square, London, United Kingdom, WC1N 1AX

e-mail:giovanna.zinzalla@pharmacy.ac.uk Contents 1. NMR spectra 2

2

10

1. NMR Spectra

3

10

4

18

5

18

6

17b

7

17b

8

11

9

11

10

15

11

15

12

19

13

19

14

12

15

12

16

16

17

16

18

20

19

20

20

21

22

23

24

ppm (t1)0.05.0

8.26

78.

245

8.11

08.

097

8.08

77.

993

7.97

17.

938

7.74

47.

711

7.70

2

5.72

55.

712

3.37

3

3.29

73.

166

3.15

13.

135

3.12

13.

089

3.07

6

2.71

22.

703

2.46

42.

250

2.23

42.

204

2.18

81.

993

1.96

6

1.53

51.

388

1.35

41.

323

1.18

01.

136

1.05

71.

024

1.001.042.154.39

1.08

0.981.080.941.16

0.921.85

1.151.01

0.603.112.721.47

1.551.65

25

ppm (f1)50100150200

200.

510

200.

014

197.

826

196.

749

136.

375

135.

928

135.

194

135.

160

134.

245

134.

106

133.

996

127.

342

127.

174

127.

094

126.

172

125.

858

122.

152

60.7

5652

.427

51.6

2250

.543

50.2

2738

.345

32.4

9426

.562

24.4

8523

.783

20.5

83

26

ppm

8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm

8

7

6

5

4

3

2

1

0

Current Data ParametersNAME ivm1-09-12-2010-44EXPNO 11PROCNO 1

F2 - Acquisition ParametersDate_ 20101210Time 16.04INSTRUM spectPROBHD 5 mm PABBO BBOPULPROG cosygpqfTD 2048SOLVENT CDCl3NS 2DS 8SWH 3654.971 HzFIDRES 1.784654 HzAQ 0.2802164 secRG 143.7DW 136.800 usecDE 6.00 usecTE 300.1 Kd0 0.00000300 secD1 1.39800894 secd13 0.00000400 secD16 0.00010000 secIN0 0.00027360 sec

======== CHANNEL f1 ========NUC1 1HP0 7.90 usecP1 7.90 usecPL1 0.00 dBSFO1 400.1317761 MHz

====== GRADIENT CHANNEL =====GPNAM1 SINE.100GPNAM2 SINE.100GPZ1 10.00 %GPZ2 10.00 %P16 1000.00 usec

F1 - Acquisition parametersND0 1TD 50SFO1 400.1318 MHzFIDRES 73.099419 HzSW 9.134 ppmFnMODE QF

F2 - Processing parametersSI 1024SF 400.1300365 MHzWDW SINESSB 0LB 0.00 HzGB 0PC 1.40

F1 - Processing parametersSI 1024MC2 QFSF 400.1300365 MHzWDW SINESSB 0LB 0.00 HzGB 0

Sample Ref 53-ivm-24-6b

27

28

25(+/-)

29

25(+/-)

30

25(+/-)

31

25(+/-)

32

26 (+/-)

33

26 (+/-)

34

26 (+/-)

35

27(+/-)

36

27(+/-)

37

27(+/-)

38

27(+/-)

39

28 (+/-)

40

28 (+/-)

41

28 (+/-)

42

29 (+/-)

43

29 (+/-)

44

29 (+/-)

45

30 (+/-)

46

30 (+/-)

47

30 (+/-)

48

30 (+/-)

49

31a(+/-)

50

31a(+/-)

51

31a(+/-)

30a(+/-)

52

31a(+/-)

53

31b(+/-)

54

31b(+/-)

55

31b(+/-)

56

31b(+/-)

57

32(+/-)

58

32(+/-)

59

33 (+/-)

60

33 (+/-)

61

34 (+/-)

62

34 (+/-)

63

36a(+/-)

64

36a (+/-)

65

36a(+/-)

66

36b(+/-)

67

36b (+/-)