Association of intramolecular furan Diels-Alder reaction and N-acyliminium alkylation for the synthesis of pentacyclic precursor of aromathecins

Synlett

Volumn , Issue 19, 2009, Pages 3214-3218

  Pin, Frédéric ^a   Comesse, Sébastien ^a   Daïch, Adam ^a  

^a UNIVERSITÉ DU HAVRE   (France)

Author keywords

amidoalkylation; Benzoindolizino l,2 b quinolinone; Diels alder; Heterocycle; N acyliminium

Indexed keywords

FURAN; ISOINDOLE DERIVATIVE; QUINOLINE DERIVATIVE;

ALKYLATION; ARTICLE; DIASTEREOISOMER; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 72049092918     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218300     Document Type: Article

References (40)

1. Verma, R. P.; Hansch, C. Chem. Rev. 2009, 109, 213.
2. (a) Cinelli, M. A.; Morrell, A.; Dexheimer, T. S.; Scher, E. S.; Pommier, Y.; Cushman, M. J. Med. Chem. 2008, 51, 4609.
3. (b) Cheng, K.; Rahier, N. J.; Eisenhauer, B. M.; Gao, R.; Thomas, S. J.; Hecht, S. M. J. Am. Chem. Soc. 2005, 127, 838.
4. Marchand, C.; Antony, S.; Kohn, K. W.; Cushman, M.; Ioanoviciu, A.; Staker, B. L.; Burgin, A. B.; Stewart, L.; Pommier, Y. Mol. Cancer Ther. 2006, 5, 287.
5. Lin, L. Z.; Cordell, G. A. Phytochemistry 1989, 28, 1295.
6. For the first synthesis of rosettacin la, see: Walraven, H. G. M.; Pandit, U. K. Tetrahedron 1979, 36, 321.
7. (a) Dai, X.; Cheng, C.; Ding, C.; Yao, Q.; Zhang, A. Synlett 2008, 2989.
8. (b) Pin, F.; Comesse, S.; Sanselme, M.; Daïch, A. J. Org. Chem. 2008, 73, 1975.
9. Zhou, H.-B.; Liu, G.-S.; Yao, Z.-J. J. Org. Chem. 2007, 72, 6270.
10. (a) Cinelli, M. A.; Morrell, A.; Dexheimer, T. S.; Scher, E. S.; Pommier, Y.; Cushman, M. J. Med. Chem. 2008, 51, 4609.
11. (b) Xiao, X.; Antony, S.; Pommier, Y.; Cushman, M. J. Med. Chem. 2006, 49, 1408.
12. (a) Brocksom, T. J.; Nakamura, J.; Ferreira, T. J.; Brocksom, U. J. Braz. Chem. Soc. 2001, 12, 597.
13. (b) Vogel, P.; Cossy, J.; Plumet, J.; Arjona, O. Tetrahedron 1999, 55, 13521; and references cited therein.
14. For the IMFDA approaches, see: (a) Boonsombat, J.; Zhang, H.; Chughtai, M. J.; Hartung, J.; Padwa, A. J. Org. Chem. 2008, 73, 3539.
15. (b) Ikoma, M.; Oikawa, M.; Sasaki, M. Tetrahedron 2008, 64, 2740.
16. Kachkovskyi, G. O.; Kolodiazhnyi, O. I. Tetrahedron 2007, 63, 12576.
17. Padwa, A.; Crawford, K. R.; Straub, C. S. J. Org. Chem. 2006, 71, 5432; and references cited therein.
18. In this area, see: (a) Varlamov, A. V.; Boltukhina, E. V.; Zubkov, F. I.; Nikitina, E. V. J. Heterocycl. Chem. 2006, 43, 1479.
19. (b) Namboothiri, I. N. N.; Ganesh, M.; Mobin, S. M.; Cojocaru, M. J. Org. Chem. 2005, 70, 2235.
20. Zubkov, F. I.; Nikitina, E. V.; Turchin, K. F.; Aleksandrov, G. G.; Safronova, A. A.; Borisov, R. S.; Varlamov, A. V. J. Org. Chem. 2004, 69, 432.
21. Zubkov, F. I.; Nikitina, E. V.; Turchin, K. F.; Safronova, A. A.; Borisov, R. S.; Varlamov, A. V. Russ. Chem. Bull, Int. Ed. 2004, 53, 860.
22. (e) Tromp, R. A.; Brussee, J.; Van Der Gen, A. Org. Biomol. Chem. 2003, 1, 3592.
23. (f) Varlamov, A. V.; Nikitina, E. V.; Zubkov, F. I.; Shurupova, O. V.; Chernyshev, A. I. Mendeleev Commun. 2002, 12, 32.
24. (g) Jacobi, P. A.; Li, Y. J. Am. Chem. Soc. 2001, 123, 9307.
25. (h) Padwa, A.; Brodney, M. A.; Satake, K.; Straub, C. S. J. Org. Chem. 1999, 64, 4617.
26. Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595.
27. (j) Lautens, M.; Fillion, E. J. Org. Chem. 1998, 63, 647.
28. (k) Padwa, A.; Dimitroff, M.; Waterson, A. G.; Wu, T. J. Org. Chem. 1998, 63, 3986.
29. Padwa, A.; Kappe, C. O.; Cochran, J. E.; Snyder, J. P. J. Org. Chem. 1997, 62, 2786.
30. Martin, S. F.; Geraci, L. S. Tetrahedron Lett. 1988, 29, 6725.
31. Ohba, M.; Kubo, H.; Natsutani, I. Tetrahedron 2007, 63, 12689; and references cited therein.
32. Pin, F.; Comesse, S.; Garrigues, B.; Marchaím, Š.; Daïch, A. J. Org. Chem. 2007, 72, 1181.
33. (a) Ishihara, Y.; Kiyota, Y.; Goto, G. Chem. Pharm. Bull. 1990, 38, 3024.
34. (b) Mali, R. S.; Yeola, S. N. Synthesis 1986, 755.
35. ar, J = 7.0 Hz)
36. Anzini, M.; Cappelli, A.; Vomero, S.; Giorgi, G.; Langer, T.; Bruni, G.; Romeo, M. R.; Basile, A. S. J. Med. Chem. 1996, 39, 4275.
37. Roma, G.; di Braccio, M.; Balbi, A.; Mazzei, M.; Ermili, A. J. Heterocycl. Chem. 1987, 24, 329.
38. 1H NMR.
39. See, for example: Mentink, G.; Van Maarseveen, J. H.; Hiemstra, H. Org. Lett. 2002, 4, 3497.
40. 4 (376.41): C, 70.20; H, 5.36; N, 7.44. Found: C, 70.05; H, 5.16; N, 7.28.