The synthesis of 8-substituted tetracycline derivatives, the first 8- position carbon-carbon bond

Tetrahedron Letters

Volumn 41, Issue 26, 2000, Pages 5017-5020

  Koza, Darrell J ^a  

^a Mount Ida College   (United States)

Author keywords

Antibacterials; Antibiotics; Coupling reactions; Polycyclic aromatic compounds

Indexed keywords

DOXYCYCLINE FOSFATEX; TETRACYCLINE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION; REACTION ANALYSIS;

EID: 0034709669     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00768-1     Document Type: Article

References (13)

1. Petsi, J. L.; Hlavka, J. J.; Boothe, J. H. J. Med. Chem. 1962, 5, 538.
2. Mitscher, L. A. In The Chemistry of Tetracycline Antibiotics, Vol. 9; Grunewald, G. L., Ed.; Marcel Dekker: New York, 1978.
3. Beerboom, J. J.; Ursprung, J. J.; Rennhard, H. H.; Stephens, C. R. J. Am. Chem. Soc. 1960, 82, 1253.
4. Hlavka, J. J.; Boothe, J. H. In Handbook of Experimental Pharmacology, Vol. 78; Born, G. V. R.; Farah, A.; Herken, H.; Welch, A. D., Eds.; Springer-Verlag: New York, 1985.
5. Glatz, B.; Helmchen, G.; Muxfeldt, H.; Porcher, H.; Prewo, R.; Senn, J.; Stezowski, J. J.; Stojda, R. J.; White, D. R. J. Am. Chem. Soc. 1979, 101, 1198.
6. Doerschuk, A. P.; Bitler, B. A.; McCormick, J. R. D. J. Am. Chem. Soc. 1956, 78, 4687.
7. Tymiak, A. A.; Ax, H. A.; Bolgar, M. S.; Kahle, A. D.; Porbucan, M. A.; Andersen, N. H. J. Anitbiotics 1992, 45, 1899.
8. Tymiak, A. A.; Aklonis, C.; Bolgar, M. S.; Kahle, A. D.; Kirsch, D. R.; O'Sullivan, J.; Porubcan, M. A.; Principe, P.; Trejo, W. H.; Ax, H. A.; Wells, J. S.; Andersen, N. H.; Devasthale, P. V.; Telikepalli, H.; Vander Velde, D.; Zou, J.; Mitscher, L. A. J. Org. Chem. 1993, 58, 535.
9. Sum, P.; Lee, V. J.; Tally, F. Tetrahedron Lett. 1994, 12, 1835.
10. Koza, D. J. Org. Lett. 2000, 6, 815.
11. Kosugi, M.; Sasazawa, K.; Shimizu, Y.; Migita, T. Chem. Lett. 1977, 301.
12. 1H NMR (methanol d-4, 400 MHz) δ 6.94 (s, 1H), 4.47 (s, 1H), 3.77 (s, 1H), 3.54 (m, 1H), 3.16 (s, 1H), 2.96 (s, 7H), 2.81 (m, 2H), 2.58 (m, 3H), 1.47 (d, J=6.13 Hz, 3H). MS (FAB) 538 and 540 amu (isotopic pattern confirming the presence of bromine).
13. 1H NMR (methanol d-4, 400 MHz) δ 7.78 (m, 5H), 6.71 (s, 1H), 3.95 (s, 1H), 3.65 (s, 1H), 2.79 (s, 7H), 2.52 (m, 3H), 1.53 (d, J=6.41 Hz, 3H).