A Study on the Syntheses of Simple Analogs of Tetracycline and Flavonoid

Tetracycline과 Flavonoid의 간단한 유도체 합성에 관한 연구

  • Kim, Hakwon (Department of Chemistry, College of Natural Science, Kyung Hee University)
  • 김학원 (경희대학교 자연과학대학 화학과)
  • Published : 19960800

Abstract

This work describes studies aimed at the synthesis of simple analogs of antibiotic tetracycline(TC) and flavonoid. The synthesis of proposed analogs of tetracycline and flavonide has been accomplished from readily available compounds 9 and 15. The 1,3-cyclohexanedione derivative 9 was transformed to the benzoate derivative 12 followed by base-mediated intramolecular benzoylation to give the bicyclic TC-analog 13. The bicyclic TC-analog 25 and the flavonoid-analogs 26 and 27 have been prepared from the quinol derivative 15.

Keywords

References

  1. Angew. Chem. Int. Ed. v.14 Durckheimer, W.
  2. Tet. Letter Martin, W.;Hartung, H.;Urbach, H.lDurckheimer, W.
  3. Comprehensive organic chemistry v.4 Staunton, J.;Sammes, P. G.(ed.)
  4. Org. Syn. v.45 Larsen, E. H.;Lawesson, S. o.
  5. J. Org. Chem. v.46 Sanifer, R. M.;Bhattacharya, A. K.;Harris, T. M.
  6. J. Org. Chem. v.57 Kraus, G. A.;Kirihara, M.
  7. J. Chem. Soc. Perkin Trans. Ⅰ Pelliciari, R.;Fringuelli, R.;Sisani, E.;Curni, M.
  8. Tet. Letter v.21 Kirchlechner, R.;Rogalski, W.
  9. J. Org. Chem. v.39 Shah, V. R.;Bose, J. L.;Shah, R. C.
  10. Burger's Medicinal Cdhemistry(4th ed.) Manfield, E. Wolff(ed.)
  11. J. Org. Chem. v.50 Rathke, M.;Nowak, M.
  12. J. Adm. Chem. Soc. v.90 Korst, J. J.;David, J.;Butler, K.;Bfianco, E. J.;Conover, L. H.;Woodward, R. B.
  13. J. Chem. Soc. Perkin Trans. Ⅰ Chorn, T. A.;Giles, R. G. F.;Green, I. R.;Hugo, V. I.;Mitchell, P. R. K.;Yorke, S. C.
  14. 논문초록 제75차 대한화학회 춘게학술회의 포스터발표 김학원;윤병훈;이은경
  15. J. Am. Chem. Soc. v.87 Muxfeldt, H.;Rogalski, W.
  16. Investigational New Drugs v.4 Corbet, T. H.;Bissery, M. C.;Wozniak, A.;Plowman, J.;Polin, L.;Tapazoglou, E.;Dieckman, J.;Valeriote, F.