3026
Y. C. Rajan, C. C. Kanakam / Tetrahedron Letters 49 (2008) 3023–3026
4. (a) Noda, Y.; Wantanabe, M. Helv. Chim. Acta 2002, 85, 3473; (b)
Hodgetts, K. J. Tetrahedron 2005, 61, 6860.
5. (a) Nakib, T. A.; Bezjak, V.; Meegan, M. J.; Chandy, R. Eur. J. Med.
Chem. 1990, 25, 55; (b) Santhosh, K. C.; Balasubramanian, K. K.
Tetrahedron Lett. 1991, 32, 7727; (c) Mandal, P.; Venkateswaran, R.
V. J. Chem. Res. (S) 1998, 88.
6. (a) Barlocco, D.; Cignarella, G.; Curzu, M. M. Synthesis 1985, 876;
(b) Jain, A. C.; Tyagi, O. D.; Saksena, R. Indian J. Chem. 1989, 15; (c)
Valenti, P.; Belluti, F.; Rampa, A.; Bisi, A. Synth. Commun. 1999, 29,
3895; (d) Draper, R. W.; Hu, B.; Iyer, R. V.; Li, X.; Lu, Y.; Rahman,
M.; Vater, E. J. Tetrahedron 2000, 56, 1811.
7. (a) Loubinoux, B.; Colin, J. L.; Antonot-Colin, B. Tetrahedron 1987,
43, 93; (b) Narkhede, D. D.; Iyer, P. R.; Iyer, C. S. R. Tetrahedron
1990, 46, 2031; (c) Srikanth, N.; Kon, O.-L.; Ng, S.-C.; Sim, K.-Y. J.
Chem. Res. (S) 1997, 202.
8. Lipinski, C. A.; Aldinger, C. E.; Beyer, T. A.; Bordne, J.; Burdi, D. F.;
Bussolotti, D. L.; Inskeep, P. B.; Siegel, T. W. J. Med. Chem. 1992,
35, 2169.
9. (a) Okuro, K.; Alpe, H. J. Org. Chem. 1997, 62, 1566; (b) Grigg, R.;
Liu, A.; Shaw, D.; Suganthan, S.; Woodall, D. E.; Yoganathan, G.
Tetrahedron Lett. 2000, 41, 7125.
10. (a) Loiodice, F.; Longo, A.; Bianco, P.; Tirtirella, V. Tetrahedron:
Asymmetry 1995, 6, 1001; (b) Woydowski, K.; Liebscher, J. Synthesis
2000, 1444; (c) Tanada, Y.; Mori, K. Eur. J. Org. Chem. 2001, 1963.
11. (a) Vicario, J. L.; Badia, D.; Dominguez, E.; Rodriguez, M.; Carrillo,
L. Tetrahedron Lett. 2000, 41, 8297; (b) Vicario, J. L.; Badia, D.;
Carrillo, L. Tetrahedron: Asymmetry 2003, 14, 489.
21.3, 68.0, 118.3, 123.3, 124.7, 125.0, 129.2, 128.6, 129.4,
130.2, 130.5, 131.7, 137.1, 140.0, 154.3, 183.0; MS (EI)
m/z 598 [M+]; mp: 200–203 °C; C42H30O4 Anal. Calcd:
C, 84.26; H, 5.05. Found: C, 84.20; H, 5.16.
Bis-chromanone 6c: Yield: 64%; IR (KBr, cmꢂ1): 1662;
1H NMR (300 MHz, CDCl3): d 3.70 (s, 6H), 5.17 (d, 2H,
J = 6.0), 5.23 (d, 2H, J = 6.6 Hz), 6.76–7.94 (m, 18H),
8.69 (s, 2H); 13C NMR (100 MHz, CDCl3): d 55.3, 68.0,
113.5, 114.2, 118.1, 123.2, 124.7, 126.9, 129.3, 130.2,
132.2, 133.2, 136.9, 137.8, 154.1, 160.8, 183.1; MS (EI)
630 [M+]; mp: 178–181 °C; C42H30O6 Anal. Calcd: C,
79.98; H, 4.79. Found: C, 79.84; H, 4.70.
Bis-chromanone 6d: Yield: 66%; IR (KBr, cmꢂ1) 1667;
1H NMR (300 MHz, CDCl3):
d
5.15 (d, 2H,
J = 10.4 Hz), 5.22 (d, 2H, J = 10.8 Hz), 6.82–7.94 (m,
18H), 8.61 (s, 2H);13C NMR (75 MHz, CDCl3): d 68.0,
118.2, 120.0, 123.3, 124.9, 126.9, 128.5, 129.5, 130.2,
130.5, 131.4, 132.0, 133.3, 134.8, 137.0, 138.5, 154.1,
183.1; MS (EI) 638 [M+]; mp: 163–166 °C; C40H24Cl2O4
Anal. Calcd: C, 75.12; H, 3.78. Found: C, 75.19; H, 3.69.
References and notes
12. Loubinoux, B.; Viriot-Chauveau, C.; Sinnes, J. L. Tetrahedron Lett.
1992, 33, 2145.
1. (a) The Flavonoids. Advances in Research Since 1980; Harborne, J. B.,
Ed.; Chapman and Hall: New York, 1988; (b) Harborne, J. B.;
Williams, C. A. Nat. Prod. Rep. 1995, 12, 639; (c) Chang, L. C.;
Kinghorn, A. D. In Bioactive Compounds from Natural Sources:
Isolation Characterization and Biological Properties; Tringali, C., Ed.;
Taylor & Francis Ltd: London, 2001. Chapter 5; (d) Flavonoids:
Chemistry, Biochemistry and Applications; Andersen, Ø. M., Mark-
ham, K. R., Eds.; Taylor & Francis Ltd: London, 2006.
13. (a) Davis, F. A.; Chen, B. C. J. Org. Chem. 1993, 58, 1751; (b)
Woydowski, K.; Ziemer, B.; Liebscher, J. J. Org. Chem. 1999, 64,
3489; (c) Hansen, K. B.; Rabbat, P.; Springfield, S. A.; Devine, P. N.;
Grabowski, E. J. J.; Reider, P. J. Tetrahedron Lett. 2001, 42, 8743.
14. (a) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002,
124, 10298; (b) Enders, D.; Breuer, K.; Runsink, J.; Teles, J. H. Helv.
Chim. Acta 1996, 79, 1899.
15. Biddle, M. M.; Lin, M.; Scheidt, K. A. J. Am. Chem. Soc. 2007, 129,
3830.
16. (a) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52,
8001; (b) Ciganek, E. Org. React. 1997, 51, 201; (c) Drewes, S. E.;
Roos, G. H. P. Tetrahedron 1988, 44, 4653.
17. Rajan, Y. C.; Kanakam, C. C.; Selvam, S. P.; Murugaesan, K.
Tetrahedron Lett. 2007, 48, 8562.
18. Van Es, J. J. G. S.; Biemans, H. A. M.; Meijer, E. W. Tetrahedron:
Asymmetry 1997, 8, 1825.
2. (a) Chen, H. Y.; Dykstra, K. D.; Birzin, E. T.; Frisch, K.; Chan, W.;
Yang, Y. T.; Mosley, R. T.; DiNinno, F.; Rohrer, S. P.; Schaeffer, J.
M.; Hammond, M. L. Bioorg. Med. Chem. Lett. 2004, 14, 1417; (b)
Tan, Q.; Blissard, T. A.; Morgan, J. D.; Birzin, E. T.; Chan, W.;
Yang, Y. T.; Pai, L.-Y.; Hayes, E. C.; DaSilva, C. A.; Warrier, S.;
Yudkovitz, J.; Wilkinson, H. A.; Sharma, N.; Fitzgerald, P. M. D.;
Li, S.; Colwell, L.; Fisher, J. E.; Adamski, S.; Reszka, A. A.; Kimmel,
D.; DiNinno, F.; Freedman, P.; Schaeffer, J. M.; Hammond, M. L.
Bioorg. Med. Chem. Lett. 2005, 15, 1675.
19. Basavaiah, D.; Bakthadoss, M.; Pandiaraju, S. J. Chem. Soc., Chem.
Commun. 1998, 1639.
20. Bucholz, R.; Hoffmann, H. M. R. Helv. Chim. Acta 1991, 74, 1213.
3. (a) Ramadas, S.; Krupadanam, G. L. D. Tetrahedron: Asymmetry
2004, 15, 3381; (b) Rakosi, M.; Tokes, A. L.; Bognar, R. Tetrahedron
Lett. 1970, 26, 2305.