A concise approach to 5-substituted-4-pyrones from kojic acid

Tetrahedron Letters

Volumn 44, Issue 39, 2003, Pages 7349-7351

  Kamino, Tomoyuki ^a   Kuramochi, Kouji ^a   Kobayashi, Susumu ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 PYRONE DERIVATIVE; KOJIC ACID;

ACYLATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; HECK REACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

LATEOLABRAX JAPONICUS;

EID: 0042381717     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01836-7     Document Type: Article

References (22)

1. (a) Sassa T., Nukina M., Suzuki Y. Agric. Biol. Chem. 55:1991;2415-2416.
2. (b) Wang C.-Y., Wang B.-G., Brauers G., Guan H.-S., Proksch P., Ebel R. J. Nat. Prod. 65:2002;772-775.
3. (c) Manker D.C., Faulkner D.J., Stout T.J., Clardy J. J. Org. Chem. 54:1989;5371-5374.
4. Li C.-S., Lacasse E. Tetrahedron Lett. 43:2002;3565-3568.
5. Tyvorskii V.I., Bobrov D.N., Kulinkovich O.G., Kimpe N.D., Tehrani K.A. Tetrahedron. 54:1998;2819-2826.
6. Zawacki F.J., Crimmins M.T. Tetrahedron Lett. 37:1996;6499-6502.
7. Arimoto H., Nishiyama S., Yamamura S. Tetrahedron Lett. 31:1990;5619-5620.
8. Arai M., Tomoda H., Okuda T., Wang H., Tabata N., Masuma R., Yamaguchi Y., Omura S. J. Antibiot. 55:2002;172-180.
9. Sefkow M., Kaatz H. Tetrahedron Lett. 40:1999;6561-6562.
10. 4 of kojic acid was unsuccessful, due to the formation of undesirable mono-silyl ether at C-5 in 67% yield.
11. +) 388.0624, found 388.0615.
12. +) 403.0751, found 403.0771.
13. Wulff W.D., Peterson G.A., Bauta W.E., Chan K.-S., Faron K.L., Gilbertson S.R., Kaesler R.W., Yang D.C., Murray C.K. J. Org. Chem. 51:1986;277-279.
14. de Meijere A., Meyer F.E. Angew. Chem., Int. Ed. Engl. 33:1994;2379-2411.
15. Heck reaction of 3-bromochromone was reported by Davies et al., see: Davies S.G., Mobbs B.E., Goodwin C.J. J. Chem. Soc., Perkin Trans. 1. 1987;2597-2604.
16. Suzuki A. J. Organomet. Chem. 576:1999;147-168.
17. Suzuki coupling of 5-bromopyrones prepared from furfuryl alcohols has been reported by Takao et al., see: Takao H., Endo Y., Horie T. Heterocycles. 36:1993;1803-1808.
18. Suzuki coupling of 3-bromochromones: Hoshino Y., Miyaura N., Suzuki A. Bull. Chem. Soc. Jpn. 61:1988;3008-3010.
19. Suzuki coupling of 3-iodochromone: Yokoe I., Sugita Y., Shirataki Y. Chem. Pharm. Bull. 37:1989;529-530.
20. Stille J.K. Angew. Chem., Int. Ed. Engl. 25:1986;508-524.
21. Jeanneret V., Meerpoel L., Vogel P. Tetrahedron Lett. 38:1997;543-546.
22. +) 344.1444, found 344.1453.