Synthesis of azabenzisochromanequinone antibiotics, II: 9(6)-hydroxy- 6(9)-azabenzisochromanequinones via aminoisochromanes and Meldrum's acid

Synthesis

Volumn , Issue 5, 1997, Pages 567-572

  Tödter, Carsten ^a   Lackner, Helmut ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; CHROMAN DERIVATIVE; QUINONE DERIVATIVE;

ALKYLATION; ANTIFUNGAL ACTIVITY; ARTICLE; CYCLIZATION; DEMETHYLATION; DRUG PURIFICATION; DRUG SYNTHESIS;

EID: 0030971095     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1222     Document Type: Article

References (22)

1. Tödter, C.; Lackner, H. Liebigs. Ann. 1996, 1385.
2. Tödter, C. Ph. D. Thesis, Universität Göttingen 1995.
3. (a) Schönebaum, A. Ph. D. Thesis, Universität Göttingen 1990.
4. (b) Hoffmann, B.; Schönebaum, A.; Lackner, H. Liebigs Ann. Chem. 1993, 333.
5. (c) Hoffmann, B.; Lackner, H. Liebigs Ann. 1995, 87.
6. (a) Withopf, P. Ph. D. Thesis, Universität Göttingen 1990.
7. (b) Baxter, I.; Philips, W. R. J. Chem. Soc., Perkin Trans. I 1973, 2374.
8. (a) Cassis, R.; Tapia, R.; Valderrama, J. A. Synth. Commun. 1985, 15, 125.
9. (b) Gomez-Bengoa, E.; Echavarren, A. M. J. Org. Chem. 1991, 56, 3497.
10. f 0.52; 15a: 0.59) was contaminated with several decomposition products (NMR analysis) and could not be purified.
11. Various 9-amino-6-aza-juglones have been synthesized in our group (Piechot, A. Diploma Thesis, Universität Göttingen 1994) and showed remarkable antibiotic activities.
12. Cresp, T. M.; Sargent, J. A.; Elix, J. A. J. Chem. Soc., Chem. Commun. 1972, 214.
13. Uemura, S.; Toshimitsu, A.; Okano, M. J. Chem. Soc., Perkin Trans. 1 1978, 1076.
14. 3, c ≥ 65%, t = 0 C) cause a cleavage of the methyl ether protecting groups and the formation of the corresponding quinone and of decomposition products.
15. Kraus, G. A.; Li, J.; Gordon, M.; Jensen, J. H. J. Org. Chem. 1994, 59, 2219.
16. (a) Grove, J. F.; Pople, M. J. Chem. Soc., Perkin Trans. 1 1979, 2048.
17. (b) Mori, K.; Gupta, A. K. Tetrahedron 1983, 41, 5295.
18. The γ-lactone of (aza)kalafungins is easily cleaved by hydrogenation, e.g. under formation of nanaomycin A analogues.
19. 1 the antibacterial activity of the products is generally decreased because of the lacking γ-lactone ring.
20. Juglomycin G: Lessmann, H. Ph. D. Thesis, Universität Göttingen 1993. Arizonins: Hochlowski, J. E.; Brill, G. M.; Andres, W. W.; Spanton, S.G.; McAlpine, J. B. J. Antibiotics 1987, 40, 401.
21. Juglomycin G: Lessmann, H. Ph. D. Thesis, Universität Göttingen 1993. Arizonins: Hochlowski, J. E.; Brill, G. M.; Andres, W. W.; Spanton, S.G.; McAlpine, J. B. J. Antibiotics 1987, 40, 401.
22. 3b,c