Acid catalyzed ring opening reactions of 6-deoxy-9-deoxo-9a-aza-9a-homo-erythromycin A 6,9-cyclic imino ether

Journal of Antibiotics

Volumn 51, Issue 9, 1998, Pages 893-896

  Lazarevski, Gorjana ^a   Kobrehel, Gabrijela ^a   Narancross D Signa, Amalija ^a   Banić Tomišić, Zrinka ^a   Metelko, Biserka ^b  

^a PLIVA Research Institute Ltd   (Croatia)

^b RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

[No Author keywords available]

Indexed keywords

ERYTHROMYCIN DERIVATIVE; MACROLIDE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 0031706031     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.7164/antibiotics.51.893     Document Type: Article

References (9)

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2. cross D signOKIĆ S.; G. KOBREHEL, N. LOPOTAR, B. KAMENAR, A. NAGL & D. MRVOŠ: Erythromycin series. Part 13. Synthesis and structure elucidation of 10-dihydro-10-deoxo-11 -methyl-11-azaerythromycin A. J. Chem. Research (S) 1988: 152-153, 1988
3. BRIGHT, G. M.; A. A. NAGL, J. BORDNER, K. A. DESAI, J. N. DIIBRINO, J. NOWAKOWSKA, L. VINCENT, R. M. WATROUS, F. C. SCIAVOLINO, A. R. ENGLISH, J. A. RETSEMA, M. R. ANDERSON, L. A. BRENAN, R. J. BOROVOY, C. R. CIMOCHOWSKI, J. A. FAIELLA. A. E. GIRARD, D. GIRARD, C. HERBERT, M. MANOUS & R. MASON: Synthesis, in vitro and in vivo activity of novel 9-deoxo-9a-aza-9a-homoerythromycin A derivatives; A new class of macrolide antibiotics, the azalides. J. Antibiotics 41: 1029-1047, 1988
4. WILKENING, R. R.; R. W. RATCLIFFE, G. A. Doss, K. F. BARTIZAL, A. C. GRAHAM & C. M. HERBERT: Synthesis of novel 8a-aza-8a-homoerythromycin derivatives via Beckmann rearrangement of (9Z)-erythromycin A oxime. Bio. Med. Chem. Lett. 3: 1287-1292, 1993
5. LAZAREVSKI, G.; G. KOBREHEL, B. METELKO & H. DUDDECK: Ring opening reactions of 6-deoxy-9-deoxo-9a-aza-9a-homoerythromycin A 6,9-cyclic imino ether. J. Antibiotics 49: 1066-1069, 1996
6. cross D signOKIĆ, S.; G. KOBREHEL, G. LAZAREVSKI, N. LOPOTAR, Z. TAMBURAŠEV, B. KAMENAR, A. NAGL & I. VICKOVIĆ: Erythromycin series. Part 11. Ring expansion of erythromycin A oxime by the Beckmann rearrangement. J. Chem. Soc., Perkin Trans I 1986: 1881-1890, 1986
7. Addition to carbon-hetero multiple bonds. In Advanced organic chemistry. Reactions, mechanisms, and structure. 3rd Ed., J. MARCH, pp. 780-872, John Wiley and Sons, Inc., 1985
8. NOURSE, J. G. & J. D. ROBERTS: Nuclear magnetic resonance spectroscopy. Carbon-13 spectra of some macrolide antibiotics. Substituent and conformational effects. J. Am. Chem. Soc. 97: 4584-4594, 1975
9. MARTIN, J. R.; R. S. EGAN, T. J. PERUN & A. W. GOLDSTEIN: 8-Epi-erythronolide A and its metabolic fate in fermentations of Streptomyces erythreus. Tetrahedron 29: 935-940, 1973