Synthesis of mukonine and seven further 1-oxygenated carbazole alkaloids

Synthesis

Volumn , Issue 10, 1998, Pages 1501-1505

  Bringmann, Gerhard ^a   Tasler, Stefan ^a   Endress, Heike ^a   Peters, Karl ^b   Peters, Eva Maria ^b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b MAX PLANCK INSTITUT FÜR FESTKÖRPERFORSCHUNG   (Germany)

Author keywords

Carbazole alkaloids; Homer Emmons reaction; Mukonine; Natural product

Indexed keywords

ALKALOID DERIVATIVE; CARBAZOLE DERIVATIVE; CLAUSINE E; MUKONINE; O DEMETHYLMURRAYANINE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0031785773     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-2184     Document Type: Article

References (40)

1. (a) Chakraborty, D. P. In Prog. Chem. Org. Nat. Prod., Vol. 34; Herz, W.; Grisebach, H.; Kirby, G. W.; Springer: Wien, 1977; p 299.
2. (b) Bhattacharyya, P.; Chakraborty, D. P. In Prog. Chem. Org. Nat. Prod., Vol. 52; Merz, W.; Grisebach, H.; Kirby, G. W.; Tamm, C., Ed.; Springer: Wien, 1987; p 159.
3. (c) Chakraborty, D. P.; Roy, S. In Prog. Chem. Org. Nat. Prod. Vol. 57; Merz, W.; Kirby, G. W.; Steglich, W.; Tamm, C., Ed.; Springer: Wien, 1991; p 71.
4. (d) Kapil, R. S. In The Alkaloids, Vol. 13; Manske, R. H. F., Ed.; Academic: New York, 1971; p 273.
5. Chakraborty, D. P.; Bhattacharyya, P.; Roy, S.; Bhattacharyya, S. P.; Biswas, A. K. Phytochemistry 1978, 17, 834.
6. (a) Chowdhury, B. K.; Chakraborty, D. P. Chem. Ind. (London) 1969, 549.
7. (b) Chowdhury, B. K.; Chakraborty, D. P. Phytochemistry 1971, 10, 1967.
8. Chakraborty, D. P.; Barman, B. K.; Bose, P. K. Tetrahedron 1965, 21, 681.
9. Fiebig, M.; Pezzuto, J. M.; Soejarto, D. D.; Kinghom, A. D. Phytochemistry 1985, 24, 3041.
10. Furukawa, H.; Wu, T.-S.; Ohta, T.; Kuoh, C.-S. Chem. Pharm. Bull. 1985, 33, 4132.
11. Wu, T.-S.; Huang, S.-C.; Wu, P.-L.; Teng, C.-M. Phytochemistry 1996, 43, 133.
12. Ito, C.; Katsuno, S.; Ohta, H.; Omura, M.; Kajiura, I.; Furukawa, H. Chem. Pharm. Bull. 1997, 45, 48.
13. Ngadjui, B. T.; Ayafor, J. F.; Sondengam, B. L.; Connolly, J. D. Phytochemistry 1989, 28, 1517.
14. Bhattacharyya, P.; Maiti, A. K.; Basu, K.; Chowdhury, B. K. Phytochemistry 1994, 35, 1085.
15. Chakraborty, D. P.; Das, K.; Das, B. P.; Chowdhury, B. K. Trans. Bose Res. Inst., Calcutta 1975, 38, 1;
16. Chem. Abstr. 1977, 86, 51029z.
17. Das, K. C.; Chakraborty, D. P.; Bose, P. K. Experentia 1965, 21, 340.
18. (a) Sarma, M. Sci. Cult. 1976, 42, 285;
19. Chem. Abstr. 1976, 85, 72096p.
20. (b) Sarma, M. Indian J. Exp. Biol. 1980, 18, 787;
21. Chem. Abstr. 1980, 93, 198373k.
22. Bringmann, G.; Ledermann, A.; Holenz, J.; Kao, M.-T.; Busse, U.; Wu, H. G.; François, G. Planta Med. 1998, 64, 54.
23. Bringmann, G.; Ledermann, A.; François, G. Heterocycles 1995, 40, 293.
24. (a) Crum, J. D.; Sprague, P. W. J. Chem. Soc., Chem. Commun. 1966, 13, 417.
25. (b) Chakraborty, D. P.; Chowdhury, B. K. J. Org. Chem. 1968, 33, 1265.
26. Moody, C. J. Synlett 1994, 681; and references cited therein.
27. (a) Knölker, H.-J.; Wolpert, M. Tetrahedron Lett. 1997, 38, 533; and references cited therein.
28. (b) Knölker, H.-J.; Bauermeister, M. Tetrahedron 1993, 49, 11221.
29. El-Rayyes, N. R. J. Prakt. Chem. 1974, 316, 386.
30. (a) Rizzacasa, M. A.; Sargent, M. V. Aust. J. Chem. 1987, 40, 1737.
31. (b) Tilve, S. G.; Tilve, A. S.; Desai, V. G. Synth. Commun. 1996, 26, 1921.
32. Owton, W. M.; Gallagher, P. T.; Juan-Montesinos, A. Synth. Commun. 1993, 23, 2119.
33. Grehn, L.; Ragnarsson, U. Angew. Chem. 1984, 96, 291;
34. Angew. Chem., Int. Ed. Engl. 1984, 23, 296.
35. (a) Bringmann, G.; Götz, R.; Harmsen, S.; Holenz, J.; Walter, R. Liebigs Ann. Chem. 1996, 2045.
36. (b) Boger, D. L.; McKie, J. A.; Cai, H.; Cacciari, B.; Baraldi, P. G. J. Org. Chem. 1996, 61, 1710.
37. Further details of the structure investigation are available on request from the Cambridge Crystallographic Data Centre, on quoting the depository number CCDC-101168, the names of the authors and the journal citation.
38. Andreoli, P.; Cainelli, G.; Panunzio, M.; Bandini, E.; Martelli, G.; Spunta, G. J. Org. Chem. 1991, 56, 5984.
39. Shin, C.-gi; Takahashi, N.; Yonezawa, Y. Chem. Pharm. Bull. 1990, 38, 2020.
40. 1H NMR and recrystallization could only be achieved in low yields.