An efficient synthesis of 7-hydroxy-2,6-dimethylchromeno[3,4-d]oxazol-4-one - A protected fragment of novenamine

Tetrahedron

Volumn 61, Issue 45, 2005, Pages 10683-10688

  Gammon, David W ^a   Hunter, Roger ^a   Wilson, Seanette A ^a  

^a UNIVERSITY OF CAPE TOWN   (South Africa)

Author keywords

Coumarin antibiotics; Novobiocin; Oxazoles; POCl3 pyridine; Robinson Gabriel mechanism

Indexed keywords

2,4 DIHYDROXY 3 METHYLACETOPHENONE; 2,6 DIMETHYL 7 HYDROXYCHROMENO[3,4 D]OXAZOL 4 ONE; 7 BENZYLOXY 2,6 DIMETHYLCHROMENO[3,4 D]OXAZOL 4 ONE; 7 BENZYLOXY 4 HYDROXY 8 METHYLCHROMEN 2 ONE; 7 HYDROXY 2,6 DIMETHYLCHROMENO[3,4 D]OXAZOL 4 ONE; ANTIBIOTIC AGENT; COUMARIN DERIVATIVE; ENAMINE; N (7 BENZYLOXY 4 HYDROXY 8 METHYL 2 OXO (2H) CHROMEN 3 YL)ACETAMIDE; NOVENAMINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; METHODOLOGY; PRIORITY JOURNAL;

EID: 26244464447     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.08.083     Document Type: Article

References (32)

1. H. Wallik, D.A. Harris, M.A. Reagan, M. Ruger, and H.B. Woodruff Antibiot. Annu. 3 1955-1956 909 917
2. F.K. Lin, and L.L. Coriell Antibiot. Med. 2 1956 268 276
3. B. Musicki, A.M. Periers, P. Laurin, D. Ferroud, Y. Benedetti, S. Lachaud, F. Chatreaux, J. Haesslein, A. Iltis, C. Pierre, J. Khider, N. Tessot, M. Airault, J. Demassey, P. Vicat, and M. Klich Bioorg. Med. Chem. Lett. 10 2000 1695 1699
4. G.A. Holdgate, A. Tunnicliffe, W.H.J. Ward, S.A. Weston, P.T. Barth, I.W.F. Taylor, R.A. Paupit, and D. Timms Biochemistry 36 1997 9663 9673
5. R.J. Lewis, O.M. Singh, C.V. Smith, T. Skarzynski, A. Maxwell, A.J. Wonacott, and D.B. Wigley EMBO J. 15 1996 1412 1420
6. C.L. Freel Meyers, M. Oberthur, H. Xu, L. Heide, D. Kahne, and C.T. Walsh Angew. Chem., Int. Ed. 43 2004 67 70
7. C. Albermann, A. Soriano, J. Jiang, H. Vollmer, J.B. Biggins, W.A. Barton, J. Lesniak, D.B. Nikolov, and J.S. Thorson Org. Lett. 5 2003 933 936
8. M.V. Blagosklonny Leukaemia 16 2002 455 462
9. J. Adams, and P.J. Elliot Oncogene 19 2000 6687 6692
10. C.F. Spencer, C.H. Stammer, J.O. Rodin, E. Walton, F.W. Holly, and K. Folkers J. Am. Chem. Soc. 80 1958 140 143
11. T. Patonay, G. Litkei, R. Bognar, J. Erdei, and C. Miszti Pharmazie 39 1984 86 91
12. B.P. Vaterlaus, J. Kiss, and H. Spiegelberg Helv. Chim. Acta 47 1964 381 390
13. B.P. Vaterlaus, K. Doebel, J. Kiss, A.I. Rachlin, and H. Spiegelberg Helv. Chim. Acta 49 1964 390 398
14. B.P. Vaterlaus, and H. Spiegelberg Helv. Chim. Acta 47 1964 508 514
15. A.M. Periers, P. Laurin, D. Ferroud, J. Haesslein, M. Klich, C. Dupuis-Hamelin, P. Mauvais, P. Lassaigne, A. Bonnefoy, and B. Musicki Bioorg. Med. Chem. Lett. 10 2000 161 165
16. J.W. Hinman, E.L. Caron, and H.J. Hoeksema J. Am. Chem. Soc. 79 1957 3789 3800
17. Y. Ueda, J.M. Chuang, L.B. Crast, and R.A. Partyka J. Org. Chem. 53 1988 5107 5113
18. D.W. Gammon, R. Hunter, and S. Wilson Tetrahedron Lett. 43 2002 3141 3144
19. R.A. Raphael, and P. Ravenscroft J. Chem. Soc., Perkin Trans. 1 1988 1823 1828
20. W.M. Barker, M.A. Hermodson, and K.P. Link J. Med. Chem. 14 1971 167 169
21. J. Klosa Pharmazie 8 1953 221 223
22. Okumura, K., Tanabe Seiyaku Co. JP 37004874.
23. J.R. Merchant, and M.S. Venkatesh Chem. Ind. (London) 1979 478 479
24. V. Colotta, D. Catarzi, F. Varano, L. Cecchi, G. Filacchioni, C. Martini, L. Giusti, and A. Lucacchini II Farmaco 53 1998 375 381
25. J.R. Merchant, and H.K. Desai Indian J. Chem. 11 1973 433 436
26. J.R. Merchant, M.S. Venkatesh, and G. Martyres Indian J. Chem., Sect. B 20 1981 711 712
27. H.H. Wasserman, and F.J. Vinick J. Org. Chem. 38 1973 2407 2408
28. K.C. Nicolaou, J. Hao, M.V. Reddy, P. Bheema Rao, G. Rassias, S.A. Snyder, X. Huang, D.Y.-K. Chen, W.E. Brenzovich, N. Giuseppone, P. Giannakakou, and A. O'Brate J. Am. Chem. Soc. 126 2004 12897 12906
29. A.I. Meyers, and D. Hoyer Tetrahedron Lett. 26 1985 4687 4690
30. M.K. Singh, R.S. Singh, and R.M. Singh Indian J. Chem., Sect. B 38 1999 920 924
31. V.S.C. Yeh Tetrahedron 60 2004 11995 12042
32. C.H. Stammer J. Org. Chem. 25 1960 460 461