R. S. Elias et al. / Tetrahedron Letters 49 (2008) 3049–3051
3051
0.83 (t, J = 6 Hz, 3H, CH2–CH3), 1.26 (m, 2H, CH2–CH3),
2.8. Data for ð8Þ
1.52 (m, 2H, N–CH2–CH2), 2.44 (dd, J = 16 and 4 Hz, 1H,
3-H), 2.82 (dd, J = 16 and 7 Hz, 1H, 3-H), 2.98 (m, 2H, N–
CH2), 3.73 (s, 3H, OCH3), 3.93 (s, 3H, OCH3), 4.72 (m,
1H, 2-H), 5.05 (s, 1H, 5-H), 6.67–7.27 (m, 8H, ole-
finic + Ar-H), 8.93 (s, 1H, OH), 9.37 (s, 1H, OH). Anal.
Calcd for (423) C25H29NO5: C, 70.90; H, 6.90; N, 3.31.
Found: C, 70.77; H, 7.22; N, 2.92.
Yellow powder (yield 14%) mp 190 °C. EI-MS: m/z =
1
457 (M+). H NMR (300 MHz, DMSO-d6) d 2.26 (s, 3H,
Ar-CH3), 2.65 (dd, J = 16 and 4 Hz, 1H, 3-H), 3.08 (dd,
J = 16 and 6 Hz, 1H, 3-H), 3.71 (s, 3H, OCH3), 3.72 (s,
3H, OCH3), 5.08 (s, 1H, 2-H), 5.42 (s, 1H, 5-H), 6.29 (d,
J = 16 Hz, 1H, olefinic-H), 6.60–7.22 (m, 11H, olefinic +
Ar-H), 8.96 (s, 1H, OH), 9.41 (s, 1H, OH). Anal. Calcd
for (457) C28H27NO5: C, 73.51; H, 5.95; N, 3.06. Found:
C, 73.36; H, 6.21; N, 2.86.
2.5. Data for ð5Þ
Yellow powder (yield 7%) mp 130 °C. CIMS: m/z = 452
(M+1)+. 1H NMR (250 MHz, DMSO-d6) d 0.78 (t,
J = 6 Hz, 3H, CH2–CH3), 1.21 (m, 6H, (CH2)3–CH3),
1.56 (m, 2H, N–CH2–CH2), 2.40 (dd, J = 16 and 4 Hz,
1H, 3-H), 2.82 (dd, J = 16 and 7 Hz, 1H, 3-H), 2.99 (m,
2H, N–CH2), 3.74 (s, 3H, OCH3), 3.80 (s, 3H, OCH3),
4.71 (m, 1H, 2-H), 5.05 (s, 1H, 5-H), 6.65–7.24 (m, 8H, ole-
finic + Ar-H). The OH protons could not be seen in the
spectrum of this compound. Anal. Calcd for (452)
C27H33NO5: C, 71.82; H, 7.37; N, 3.10. Found: C, 71.92;
H, 7.69; N, 2.85.
References and notes
1. Harmata, M.; Lee, D. R. ARKIVOC 2007, V, 91.
2. Comins, D. L. J. Heterocycl. Chem. 1999, 36, 1491.
3. Joseph, S.; Comins, D. L. Curr. Opin. Drug Discovery Dev. 2002, 5,
870.
4. Harmata, M.; Lee, D. R. J. Am. Chem. Soc. 2002, 124, 14328.
5. Harmata, M.; Lee, D. R.; Barnes, C. L. Org. Lett. 2005, 7, 1881.
6. Etexebarria, J.; Vicario, J. L.; Badia, D.; Corrillo, L. J. Org. Chem.
2004, 69, 2588.
7. Tewari, N.; Katiyar, D.; Tiwari, V. K.; Tripathi, R. P. Tetrahedron
Lett. 2003, 44, 6639.
8. Guo, H.; Ding, K. Tetrahedron Lett. 2003, 44, 7103.
9. Mancheno, O. G.; Arrayas, R. G.; Carretero, J. C. J. Am. Chem. Soc.
2004, 126, 456.
10. Comins, D. L.; Joseph, S. P.; Goehring, R. R. J. Am. Chem. Soc.
1994, 166, 4719.
11. Comins, D. L.; Goehring, R. R.; Joseph, S. P.; O Connor, S. J. Org.
Chem. 1990, 55, 2574.
12. Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocycles;
JAI Press, 1996; Vol. 2, p 251.
13. Ohts, H.; Xiao, Z.; Ishida, J.; Nagai, M.; Wang, H.-K.; Itokawa, H.;
Su, C.-Y.; Shih, C.; Chiang, T.; Chang, E.; Li, Y.; Tsai, M.-Y.;
Chang, C.; Lee, K.-H. J. Med. Chem. 2002, 45, 5037.
14. Masuda, T.; Mackawa, T.; Hidaka, K.; Bando, H.; Takeda, Y.;
Yamaguchi, H. J. Agric. Food Chem. 2001, 49, 2539.
15. Balasubramanian, K. J. Agric. Food Chem. 2006, 54, 3512.
16. Park, S. Y.; Kim, D. S. J. Nat. Prod. 2002, 56, 1227.
17. Asai, A.; Magasawa, T. J. Nutr. 2001, 131, 2932.
18. Leu, T. H.; Maa, M. C. Curr. Med. Chem. Anti-Cancer Agents 2002,
2, 357.
19. Shishodia, S.; Potdar, P.; Gairola, C. G.; Aggarwal, B. B. Carcino-
genesis 2003, 24, 1269.
20. Lim, G. P.; Chu, T.; Yang, F.; Beech, W.; Frautschy, S. A.; Cole, C.
M. J. Neurosci. 2001, 21, 8370.
21. Sugiyama, N.; Yamamoto, M.; Kashima, Ch. Bull. Chem. Soc. Jpn.
1970, 43, 3937.
22. Gayaprakasha, G. K.; Rao, L. J. M.; Sakariah, K. K. J. Agric. Food
Chem. 2002, 50, 3668.
2.6. Data for ð6Þ
Yellow powder (yield 13%) mp 128 °C. CIMS:
m/z = 458 (M+1)+. 1H NMR (250 MHz, DMSO-d6) d
2.40 (dd, J = 16 and 4 Hz, 1H, 3-H), 2.82 (dd, J = 16
and 7 Hz, 1H, 3-H), 3.71 (s, 3H, OCH3), 3.79 (s, 3H,
OCH3), 4.20 (s, 2H, N–CH2), 4.72 (m, 1H, 2-H), 5.18 (s,
1H, 5-H), 6.71–7.37 (m, 13H, olefinic + Ar-H), 9.00 (s,
1H, OH), 9.43 (s, 1H, OH). Anal. Calcd for (457)
C28H27NO5: C, 73.51; H, 5.95; N, 3.06. Found: C, 73.08.;
H, 6.22; N, 2.87.
2.7. Data for ð7Þ
Yellow powder (yield 13%) mp 111 °C. EI-MS:
m/z = 443 (M) +. H NMR (300 MHz, DMSO-d6) d 2.60
1
(dd, J = 16 and 4 Hz, 1H, 3-H), 3.00 (dd, J = 16 and
6 Hz, 1H, 3-H), 3.70 (s, 3H, OCH3), 3.71 (s, 3H, OCH3),
5.08 (m, 1H, 2-H), 5.42 (s, 1H, 5-H), 6.70–7.36 (m, 13H,
olefinic + Ar-H). The OH protons could not be seen in
the spectrum of this compound. Anal. Calcd for (443)
C27H25NO5: C, 73.12; H, 5.68; N, 3.16. Found: C, 72.98;
H, 5.93; N, 2.92.