A facile total synthesis of rutaecarpine

Tetrahedron Letters

Volumn 45, Issue 5, 2004, Pages 997-999

  Chavan, Subhash P ^a   Sivappa, R ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Dieckmann condensation decarboxylation; Indoloquinazoline alkaloid; Rutaecarpine

Indexed keywords

9,10,11,12 TETRAHYDRO 4H PYRIDO[2,1 B]QUINAZOLINE 4,9 DIONE; ALKALOID; ESTER DERIVATIVE; QUINAZOLINE DERIVATIVE; QUINAZOLINONE DERIVATIVE; RUTAECARPINE; UNCLASSIFIED DRUG;

ARTICLE; DECARBOXYLATION; DIECKMANN REACTION; DRUG SYNTHESIS;

EID: 0345761292     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.11.090     Document Type: Article

References (27)

1. Asahima Y., Kashiwaki K. J. Pharm. Soc. Jpn. 35:1915;1293.
2. Bergman J. Brossi A.R. The Alkaloids. Vol. 21:1983;29 Academic, NewYork.
3. Ikuta A., Urabe H., Nakamura T. J. Nat. Prod. 61:1998;1012.
4. Chu J.H. Sci. Record. 4:1951;279. Chem. Abstr. 1952, 46, 11589b.
5. Li H.-T., Houng H.-I. Yao Hsueh Hsueh Pao. 13:1966;265. Chem. Abstr. 1966, 65, 3922c.
6. Amin A.H., Mehta D.R., Samarth S.G. Prog. Drug. Res. 14:1970;218.
7. Johne S. Prog. Drug. Res. 26:1982;259.
8. Kiss A., Kokosi J., Rotter R., Hemecz I. Tetrahedron. 56:2000;7987. and references cited therein.
9. Yang L.M., Lin S.-J., Lin L.-C., Kuo Y.-H. Chin. Pharm. J. 51:1999;219.
10. Yang L.M., Chen C.-F., Kuo H.-L. Bioorg. Med. Lett. 5:1995;465.
11. Kametani T., Loc C.V., Higa T., Koizumi M., Ihara M., Fukumoto K. J. Am. Chem. Soc. 99:1977;2306.
12. Bergman J., Bergman S. Heterocycles. 16:1981;2347.
13. Bergman J., Bergman S. J. Org. Chem. 50:1985;1246.
14. Eguchi S., Takeuchi H., Matsushita Y. Heterocycles. 33:1992;153.
15. Kaneko C., Chiba T., Kasaki K., Miwa C. Heterocycles. 23:1985;1385.
16. Kokosi J., Hermecz I., Szasz G., Meszaros Z. Tetrahedron Lett. 22:1981;4861.
17. Mohanta P.K., Kim K. Tetrahedron Lett. 43:2002;3993.
18. Lee E.S., Park J.G., Jahng Y. Tetrahedron Lett. 44:2003;1883. and references cited therein.
19. For a recent review on the Fischer indole synthesis, see: Hughes D.L. Org. Prep. Proced. Int. 5:1993;607.
20. Kokosi J., Hermecz I., Podanyi B., Szasz G., Meszaros Z. J. Heterocycl. Chem. 22:1985;1373.
21. Hermecz I., Kokosi J., Horvath A., Vasavari D.I., Podanyi B., Szasz G., Meszaros Z. J. Heterocycl. Chem. 24:1987;1045.
22. Hermecz I., Kokosi J., Vasavari D.I., Horvath A., Szasz G., Meszaros Z. F.E.C.S. Int. Conf. Chem. Biotechnol. Biol. Act. Nat. Prod. Vol. 5:1987;VCH, Weinheim, Germany. p 332; Chem. Abstr. 1989, 110, 231939.
23. Hermecz I., Kokosi J., Vasavari D.I., Podanyi B., Szasz G. Heterocycles. 37:1994;903.
24. For preparative routes to N-aryl hydrazones, see: Robinson B. The Fischer Indole Synthesis. 1982;John Wiley & Sons, Chichester. pp 48-59.
25. Smith P.A.S. Derivatives of Hydrazine and Other Hydronitrogens Having N-N Bonds. 2nd ed. 1983;The Benjamin/Cummings Publishing Company, Reading, MA. Chapter 2.
26. Venuti M.C. Synthesis. 1982;266.
27. Wang H., Ganesan A. J. Org. Chem. 65:2000;1022.