K. Odlo et al. / Tetrahedron Letters 47 (2006) 1101–1103
1103
10. Stork, G.; Takahashi, T. J. Am. Chem. Soc. 1977, 99,
1275.
Acknowledgment
11. Spectral data of selected compounds: 3-bromo-6-meth-
Financial support to K.O. from the School of Phar-
macy, University of Oslo, is gratefully acknowledged.
1
oxybenzene-1,2-diol (5): white solid; H NMR (300 MHz,
CDCl3): d 6.98 (d, J 8.9 Hz, 1H), 6.42 (d, J 8.9 Hz, 1H),
5.57 (s, 1H), 5.52 (s, 1H), 3.87 (s, 3H); 13C NMR (75 MHz,
CDCl3): d 146.6, 141.0, 133.5, 122.2, 104.4, 101.6, 56.3;
HRMS calcd for C7H7BrO3 (M+): 217.9579, found
217.9586; 1-bromo-4-methoxy-2,3-bis(methoxymethoxy)-
benzene (6): colorless oil; 1H NMR (300 MHz, CDCl3):
d 7.23 (d, J 9.0 Hz, 1H), 6.59 (d, J 9.0 Hz, 1H), 5.18 (s,
2H), 5.11 (s, 2H), 3.82 (s, 3H), 3.64 (s, 3H), 3.57 (s, 3H);
13C NMR (75 MHz, CDCl3): d 153.3, 148.2, 140.0, 127.5,
108.9, 108.7, 99.4, 98.7, 58.1, 57.5, 56.1; HRMS calcd for
C11H15BrO5 (M+): 306.0103, found 306.0112; 1-iodo-4-
methoxy-2,3-bis(methoxymethoxy)benzene (7): yellow oil;
1H NMR (300 MHz, CDCl3): d 7.47 (d, J 8.9 Hz, 1H),
6.51 (d, J 8.9 Hz, 1H), 5.19 (s, 2H), 5.11 (s, 2H), 3.83 (s,
3H), 3.67 (s, 3H), 3.58 (s, 3H); 13C NMR (75 MHz,
CDCl3): d 154.4, 150.7, 139.1, 133.5, 110.0, 99.5, 98.7,
81.6, 58.6, 57.5, 56.1; HRMS calcd for C11H15IO5 (M+):
353.9964, found 353.9966; 1-methoxy-2,3-bis(methoxy-
methoxy)-4-((3,4,5-trimethoxyphenyl)-ethynyl)benzene
References and notes
1. Pettit, G. R.; Singh, S. B.; Niven, M. L.; Hamel, E.;
Schmidt, J. M. J. Nat. Prod. 1987, 50, 119.
2. (a) Lin, C. M.; Singh, S. B.; Chu, P. S.; Dempcy, R. O.;
Schmidt, J. M.; Pettit, G. R.; Hamel, E. Mol. Pharmacol.
1988, 34, 200; (b) Pettit, G. R.; Toki, B. E.; Herald, D. L.;
Boyd, M. R.; Hamel, E.; Pettit, R. K.; Chapuis, J. C. J.
Med. Chem. 1999, 42, 1459; (c) Pettit, G. R.; Grealish, M.
P.; Herald, D. L.; Boyd, M. R.; Hamel, E.; Pettit, R. K. J.
Med. Chem. 2000, 43, 2731.
3. Jordan, A.; Hadfield, J. A.; Lawrence, N. J.; McGown, A.
T. Med. Res. Rev. 1998, 18, 259.
4. (a) Nandy, P.; Banerjee, S.; Gao, H.; Hui, M. B. V.; Lien,
E. J. Pharm. Res. 1991, 8, 776; (b) Hadfield, J. A.;
McGown, A. T. Synth. Commun. 1998, 28, 1421; (c)
Lawrence, N. J.; Ghani, F. A.; Hepworth, L. A.; Hadfield,
J. A.; McGown, A. T.; Pritchard, R. G. Synthesis 1999, 9,
1656; (d) Brown, M. L.; Rieger, J. M.; Macdonald, T. L.
Bioorg. Med. Chem. 2000, 8, 1433; (e) Nam, N.-H.; Kim,
Y.; You, Y.-J.; Hong, D.-H.; Kim, H.-M.; Ahn, B.-Z.
Bioorg. Med. Chem. Lett. 2002, 12, 1955; (f) Gaukroger,
K.; Hadfield, J. A.; Lawrence, N. J.; Nolan, S.; McGown,
A. T. Org. Biomol. Chem. 2003, 1, 3033.
5. (a) Bacher, G.; Beckers, T.; Emig, P.; Klenner, T.;
Kutscher, B.; Nickel, B. Pure Appl. Chem. 2001, 73,
1459; (b) Dzierzbicka, K.; Kolodziejczyk, A. M. Polish J.
Chem. 2004, 78, 323.
6. (a) Orsini, F.; Pelizzoni, F.; Bellini, B.; Miglierini, G.
Carbohydr. Res. 1997, 301, 95; (b) Pettit, G. R.; Lippert, J.
W., III. Anti Cancer Drug Des. 2000, 15, 203.
1
(9): yellow oil; H NMR (300 MHz, CDCl3): d 7.24 (d, J
8.7 Hz, 1H), 6.74 (s, 2H), 6.68 (d, J 8.8 Hz, 1H), 5.31 (s,
2H), 5.14 (s, 2H), 3.87 (s, 3H), 3.86 (s, 9H), 3.66 (s, 3H),
3.61 (s, 3H); 13C NMR (75 MHz, CDCl3): d 154.3, 153.1,
151.7, 139.0, 138.7, 128.6, 118.5, 110.8, 108.6, 107.8, 99.2,
98.7, 92.0, 84.9, 60.9, 57.6, 57.4, 56.1, 56.0; HRMS calcd
for C22H26O8 (M+): 418.1628, found 418.1629; combre-
tastatin A-1 (1): 1H NMR (300 MHz, CDCl3): 6.76 (d, 1H,
J 8.7 Hz), 6.59 (d, 1H, J 12.2 Hz), 6.53 (d, 1H, J 12.0 Hz),
6.52 (s, 2H), 6.38 (d, 1H, J 8.6 Hz), 5.41 (s, 2H), 3.86 (s,
3H), 3.83 (s, 3H), 3.67 (s, 6H); 152.8, 146.3, 141.6, 137.3,
132.6, 132.5, 130.3, 124.0, 120.3, 117.8, 105.9, 102.9, 60.9,
56.2, 55.8; combretastatin B-1 (2): 1H NMR (300 MHz,
CD3OD): 6.44 (s, 2H), 6.43 (d, J 8.4 Hz, 1H), 6.35 (d, J
8.4 Hz, 1H), 3.79 (s, 3H), 3.76 (s, 6H), 3.71 (s, 3H), 2.80 (s,
4H); 13C NMR (75 MHz, CDCl3): 154.1, 148.0, 144.8,
140.2, 137.0, 135.0, 122.8, 120.8, 106.9, 103.8, 61.1, 56.6,
56.5, 37.7, 33.3.
7. Bui, V. P.; Hudlicky, T.; Hansen, T. V.; Stenstrøm, Y.
Tetrahedron Lett. 2002, 43, 2839.
8. Hansen, T. V.; Skattebøl, L. Tetrahedron Lett. 2005, 46,
3357.
9. (a) Hansen, T. V.; Skattebøl, L. Org. Synth. 2005, 82, 64;
(b) Hofsløkken, N. U.; Skattebøl, L. Acta Chem. Scand.
1999, 53, 258.
12. Colvin, E. W.; Hamill, B. J. J. Chem. Soc., Chem.
Commun. 1973, 151.
13. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron
Lett. 1975, 16, 4467.