Synthesis of an analogue of lavendamycin and of conformationally restricted derivatives by cyclization via a hemiaminal intermediate

Tetrahedron Letters

Volumn 48, Issue 34, 2007, Pages 6014-6018

  Nourry, Arnaud ^a   Legoupy, Stéphanie ^a   Huet, François ^a  

^a UCO2M   (France)

Author keywords

Cyclization; Hemiaminal; Lavendamycin; Nitrogen heterocycles; Topoisomerase

Indexed keywords

ACETOACETIC ACID DERIVATIVE; ACETOACETIC ACID METHYL ESTER; AMINOBENZALDEHYDE; BENZALDEHYDE DERIVATIVE; LAVENDAMYCIN; LAVENDAMYCIN DERIVATIVE; NATURAL PRODUCT; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DESILYLATION; OXIDATION REDUCTION REACTION; PICTET SPENGLER REACTION; SYNTHESIS;

EID: 34547165546     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.100     Document Type: Article

References (53)

1. Doyle T.W., Balitz D.M., Grulich R.E., Nettleton D.E., Gould S.J., Tann C.-H., and Moews A.E. Tetrahedron Lett. 22 (1981) 4595-4598
2. Balitz D.M., Bush J.A., Bradner W.T., Doyle T.W., O'Herron F.A., and Nettleton D.E. J. Antibiot. 35 (1982) 259-265
3. Riou J.-F., Helissey P., Grondard L., and Giorgi-Renault S. Mol. Pharmacol. 40 (1991) 699-706
4. Hibino S., Okazaki M., Sato K., Morita I., and Ichikawa M. Heterocycles 20 (1983) 1957-1958
5. Hibino S., Okazaki M., Ichikawa M., Sato K., and Ishizu T. Heterocycles 23 (1985) 261-264
6. Kende A.S., and Ebetino F.H. Tetrahedron Lett. 25 (1984) 923-926
7. Kende A.S., Ebetino F.H., Battista R., Boatman R.J., Lorah D.P., and Lodge E. Heterocycles 21 (1984) 91-106
8. Rao A.V.R., Chavan S.P., and Sivadasan L. Indian J. Chem. B 23B (1984) 496-497
9. Rao A.V.R., Chavan S.P., and Sivadasan L. Tetrahedron 42 (1986) 5065-5071
10. Boger D.L., and Panek J.S. Tetrahedron Lett. 25 (1984) 3175-3178
11. Boger D.L., Duff S.R., Panek J.S., and Yasuda M. J. Org. Chem. 50 (1985) 5782-5789
12. Boger D.L., Duff S.R., Panek J.S., and Yasuda M. J. Org. Chem. 50 (1985) 5790-5795
13. Molina P., Fresneda P.M., and Cánovas M. Tetrahedron Lett. 33 (1992) 2891-2894
14. Molina P., Murcia F., and Fresneda P.M. Tetrahedron Lett. 35 (1994) 1453-1456
15. Behforouz M., Gu Z., Cai W., Horn M.A., and Ahmadian M. J. Org. Chem. 58 (1993) 7089-7091
16. Behforouz M., Haddad J., Cai W., Arnold M.B., Mohammadi F., Sousa A.G., and Horn M.A. J. Org. Chem. 61 (1996) 6552-6555
17. Ciufolini M.A., and Bishop M.J. J. Chem. Soc., Chem. Commun. (1993) 1463-1464
18. Rocca P., Marsais F., Godard A., and Quéquiner G. Tetrahedron Lett. 34 (1993) 2937-2940
19. Boger D.L., and Yasuda M. Heterocycles 24 (1986) 1067-1073
20. Boger D.L., Yasuda M., Mitscher L.A., Drake S.D., Kitos P.A., and Thompson S.C. J. Med. Chem. 30 (1987) 1918-1928
21. Hibino S., Okazaki M., Ichikawa M., Sato K., Motoshima A., and Ueki H. Chem. Pharm. Bull. 34 (1986) 1376-1379
22. Hafuri Y., Takemori E., Oogose K., Inouye Y., Nakamura S., Kitahara Y., Nakahara S., and Kuno A. J. Antibiot. 41 (1988) 1471-1478
23. Godard A., Rocca P., Fourquez J.-M., Rovera J.-C., Marsais F., and Quéquiner G. Tetrahedron Lett. 34 (1993) 7919-7922
24. Molina P., Fresneda P.M., García-Zafra S., and Almendros P. Tetrahedron Lett. 35 (1994) 8851-8854
25. Haffer G., Nickisch K., and Tilstam U. Heterocycles 48 (1998) 993-998
26. Barbier C., Joissains A., Commerçon A., Riou J.-F., and Huet F. Heterocycles 53 (2000) 37-48
27. Behforouz, M.; Merriman, R. L. U.S. Patent. No 5,552,611 1996.
28. Behforouz, M.; Merriman, R. L. U.S. Patent. No 5,646,150 1997.
29. Behforouz M., Cai W., Stocksdale M.G., Lucas J.S., Jung J.Y., Briere D., Wang A., Katen K.S., and Behforouz N.C. J. Med. Chem. 46 (2003) 5773-5780
30. Fang Y., Linardic C.M., Richardson D.A., Cai W., Behforouz M., and Abraham R. Mol. Cancer Ther. 2 (2003) 517-526
31. Seradj H., Cai W., Erasga N.O., Chenault D.V., Knuckles K.A., Ragains J.R., and Behforouz M. Org. Lett. 6 (2004) 473-476
32. Hassani M., Cai W., Holley D.C., Lineswala J.P., Maharjan B.R., Ebrahimian G.R., Seradj H., Stocksdale M.G., Mohammadi F., Marvin C.C., Gerdes J.M., Beall H.D., and Behforouz M. J. Med. Chem. 48 (2005) 7733-7749 See also several of the Ref. 4
33. For a review see:. Du W. Tetrahedron 59 (2003) 8649-8687
34. Fang S.-D., Wang L.-K., and Hecht S.M. J. Org. Chem. 58 (1993) 5025-5027
35. Smith L.I., and Opie J.W. Org. Synth. Coll. Vol. 3 (1955) 56-57
36. Thummel R.P., Chirayil S., Hery C., Lim J.-L., and Wang T.-L. J. Org. Chem. 58 (1993) 1666-1671
37. Ehrig, V.; Bien, H. S.; Klauke, E.; Schutze, D. I. West German Pat. No. 2,730,061 1979.
38. Cheng C.-C., and Yan S.-J. Org. React. 28 (1982) 37-201
39. 2O.
40. Mitsunobu O. Synthesis (1981) 1-28
41. Hughes D.L. Org. React. 42 (1992) 335-656
42. Basavaiah D., Reddy R.M., Kumaragurubaran N., and Sharada D.S. Tetrahedron 58 (2002) 3693-3697
43. Dess D.B., and Martin J.C. J. Am. Chem. Soc. 113 (1991) 7277-7278
44. Frigerio M., Santagostino M., and Sputore S. J. Org. Chem. 64 (1999) 4537-4538
45. Suni V., Kurup M.R.P., and Nethaji M. J. Mol. Struct. 749 (2005) 177-182 and references cited therein
46. El Mail R., Garralda M.A., Hernández R., Ibarlucea L., Pinilla E., and Torres M.R. Organometallics 19 (2000) 5310-5317
47. Hayakawa K., Yasukouchi T., and Kanematsu K. Tetrahedron Lett. 28 (1987) 5895-5898
48. Hiroya K., Itoh S., and Sakamoto T. J. Org. Chem. 69 (2004) 1126-1136
49. Brown H.C., and Heim P. J. Org. Chem. 38 (1973) 912-916
50. Kajino M., and Meguro K. Heterocycles 31 (1990) 2153-2161
51. Vasse J.-L., Levacher V., and Bourguignon J.D.G. J. Chem. Soc., Chem. Commun. (2002) 2256-2257
52. 3): δ = 8.80 (s, 1H, H-3), 8.65 (d, J = 8.2 Hz, 1H), 8.20 (br s, 1H, OH), 8.12 (d, J = 7.7 Hz, 1 H), 7.71 (ddd, J = 1.0, 8.2, 8.3 Hz, 1H), 7.50 (ddd, J = 0.7, 7.8, 7.9 Hz, 1H), 7.20-7.15 (m, 2H)...
53. -4 M for the three compounds.