Synthesis of optically pure pyrroloquinolones via Pictet-Spengler and Winterfeldt reactions

Tetrahedron Letters

Volumn 43, Issue 49, 2002, Pages 8941-8945

  Jiang, Weiqin ^a   Sui, Zhihua ^a   Chen, Xin ^a  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 NAPHTHALEN 1 YLETHYLAMINE; BETA CARBOLINE DERIVATIVE; QUINOLONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHIRALITY; DIASTEREOISOMER; DRUG SYNTHESIS; EPIMERIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION; PICTET SPENGLER REACTION; THIN LAYER CHROMATOGRAPHY; WINTERFELDT REACTION;

EID: 0037010827     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02147-0     Document Type: Article

References (29)

1. Sui, Z.; Macielag, M. J.; Guan, J.; Jiang, W.; Lanter, J. C. PCT Int. Appl. 2001 WO 0187882 Sui, Z.; Macielag, M. J. PCT Appl. WO 0187038, 2001 Sui, Z.; Guan, J.; Jiang, W.; Macielag, M. J.; Walsh, S. P.; Lanter, J. C.; Fiordeliso, J. J.; Alford, V. C., Jr.; Qiu, Y.; Patricia, K.; Bhattacharjee, S.; Lombardi, E.; Haynes-Johnson, D.; John, T. M.; Clancy, J. Abtracts of Papers, 224th ACS National Meeting, Boston, MA, United States, August 18-22, 2002, MEDI-278.
2. Sui Z., Guan J., Macielag M.J., Jiang W., Zhang S., Qiu Y., Kraft P., Bhattacharjee S., John T.M., Haynes-Johnson D., Clancy J. J. Med. Chem. 45:2002;4094-4096;
3. Jiang, W.; Sui, Z.; Macielag, M. J.; Walsh, S. P.; Fiordeliso, J. C.; Lanter, J.; Guan, J.; Qiu, Y.; Kraft, P.; Bhattacharjee, S.; Craig, E.; Haynes-Johnson, D.; John, T. M.; Clancy, J. J. Med. Chem., submitted Lanter, J. C.; Sui, Z.; Macielag, M. J.; Fiordeliso, J. J.; Jiang, W.; Qiu, Y.; Bhattacharjee, S.; Kraft, P.; John, T. M.; Haynes-Johnson, D.; Craig, E.; Clancy, J. J. Med. Chem., submitted.
4. Kawate T., Yamanaka M., Nakagawa M. Heterocycles. 50:1999;1033-1039.
5. Legseir B., Aichaoui H., Ladjama D. J. Soc. Alger. Chim. 6:1996;17-27.
6. Waldmann H., Schmidt G., Henke H., Burkard M. Angew. Chem., Int. Ed. Engl. 34:1995;2402-2403.
7. Hajipour A.R., Hantehzadeh M. J. Org. Chem. 64:1999;8475-8478.
8. Uematsu N., Fujii A., Hashiguchi S., Ikariya T., Noyori R. J. Am. Chem. Soc. 118:1996;4916-4917.
9. Nakagawa M., Kawate T., Kakikawa T., Yamada H., Matsui T., Hino T. Tetrahedron. 49:1993;1739.
10. Czerwinski K.M., Cook J.M. Adv. Heterocycl. Nat. Prod. Synth. 3:1996;217-277.
11. Cox E.D., Cook J.M. Chem. Rev. (Washington, D. C.). 95:1995;1797-1842.
12. Li J., Wang T., Yu P., Peterson A., Weber R., Soerens D., Grubisha D., Bennett D., Cook J.M. J. Am. Chem. Soc. 121:1999;6998-7010.
13. Soe T., Kawate T., Fukui N., Hino T., Nakagawa M. Heterocycles. 42:1996;347-358.
14. Ungemach F., Cook J.M. Heterocycles. 9:1978;1089-1119.
15. Harrison D.M., Sharma B. Tetrahedron. 49:1993;3165-3184.
16. Ungemach F., DiPierro M., Weber R., Cook J.M. J. Org. Chem. 46:1981;164-168.
17. Waldmann H., Schmidt G. Tetrahedron. 50:1994;11865-11884.
18. Melnyk P., Ducrot P., Thal C. Tetrahedron. 49:1993;8589-8596.
19. Comins D., Thakker P.M., Baevsky M.F., Badawi M.M. Tetrahedron. 53:1997;16327-16340.
20. Kawate T., Yamada H., Matsumizu M., Nishida A., Nakasawa M. Synlett. 1997;761-762.
21. Reddy M.S., Cook J.M. Tetrahedron Lett. 35:1994;5413-5416.
22. Winterfeldt E. Liebigs Ann. Chem. 745:1971;23-30.
23. Warneke J., Winterfeldt E. Chem. Ber. 105:1972;2120-2125.
24. Boch M., Korth T., Nelke J.M., Pike D., Radunz H., Winterfeldt E. Chem. Ber. 105:1972;2126-2142.
25. Carniaux J.-F., Kan-Fan C., Royer J., Husson H.-P. Tetrahedron Lett. 1997;2997-3000.
26. Sandrin J., Soerens D., Mokry P., Cook J. Heterocycles. 6:1977;1133-1139.
27. 1H NMR showed pure compound 4.
28. 2 459.2072; found 459.2060.
29. D=-37.9° (c 1.00, MeOH).