Total synthesis of naturally occurring 5,6,7- and 5,7,8-trioxygenated coumarins

Tetrahedron

Volumn 64, Issue 19, 2008, Pages 4438-4443

  Maes, Dominick ^a   Riveiro, Maria Eugenia ^b,c   Shayo, Carina ^b   Davio, Carlos ^c   Debenedetti, Silvia ^d   De Kimpe, Norbert ^a  

^a GHENT UNIVERSITY   (Belgium)

^b INST DE BIOL Y MED EXPERIMENTAL   (Argentina)

^c UNIVERSIDAD DE BUENOS AIRES   (Argentina)

^d FACULTAD DE CIENCIAS EXACTAS   (Argentina)

Author keywords

Coumarins; Natural products; Total synthesis; Wittig reaction

Indexed keywords

5,7,8 TRIMETHOXYCOUMARIN; ARTANIN; BENZALDEHYDE DERIVATIVE; COUMARIN DERIVATIVE; FRAXINOL; LEPTODACTYLONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; PRIORITY JOURNAL; SYNTHESIS; WITTIG REACTION;

EID: 41549165102     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.02.059     Document Type: Article

References (24)

1. Murray R.D.H. Prog. Chem. Org. Nat. Prod. 83 (2002) 673
2. Kayser O., and Kolodziej H.Z. Z. Naturforsch. 54c (1999) 169-174
3. Wu T.-S., Tsang Z.-J., Wu P.-L., Lin F.-W., Li C.-Y., Teng C.-M., and Lee K.-H. Bioorg. Med. Chem. 9 (2001) 77-83
4. Riveiro M.E., Shayo C., Monczor F., Fernández N., Baldi A., De Kimpe N., Rossi J., Debenedetti S., and Davio C. Cancer Lett. 210 (2004) 179-188
5. Kostova I. Planta Med. 58 (1992) 484
6. Abou Zeid A.H.S. Food Chem. 76 (2002) 187-195
7. Deng Y.-R., Song A.-X., and Wang H.-Q. J. Chin. Chem. Soc-TAIP 51 (2004) 629-636
8. Ishii H., Kobayashi J.-I., and Ishikawa T. Chem. Pharm. Bull. 31 (1983) 3330-3333
9. Latté K.P., Kayser O., Tan N., Kaloga M., and Kolodziej H. Z. Naturforsch. 55c (2000) 528-533
10. Wagner H., and Bladt S. Phytochemistry 14 (1975) 2061-2064
11. Kayser O., and Kolodziej H. Planta Med. 63 (1997) 508-510
12. Dean F.M., Costa A.M.B.S.R.C.S., Harborne J.B., and Smith D.M. Phytochemistry 17 (1978) 505-509
13. Ahluwalia V.K., and Prakash C. Indian J. Chem. 15B (1977) 808
14. Deshmukh M.N., Deshpande V.H., and Rao A.V.R. Phytochemistry 15 (1976) 1419
15. Szabó G., Greger H., and Hofer O. Phytochemistry 24 (1985) 537-541
16. Hepworth J.D. Coumarins (2H-1-benzopyran-2-ones). In: Katritzky A.R. (Ed). Comprehensive Heterocyclic Chemistry II Vol. 5 (1996), Elsevier, Amsterdam 417-425
17. Harayama T., Nakatsuka K., Katsuno K., Nishioka H., Murakami K., Fujii M., Hayashida N., and Takeuchi Y. Chem. Express 8 (1993) 245-248
18. Harayama T., Nakatsuka K., Nishioka H., Murakami K., Ohmori Y., Takeuchi Y., Ishii H., and Kenmotsu K. Heterocycles 38 (1994) 2729-2738
19. Demyttenaere J., Vervish S., Debenedetti S., Coussio J., Maes D., and De Kimpe N. Synthesis 11 (2004) 1844-1848
20. Maes D., Vervish S., Debenedetti S., Davio C., Mangelinckx S., Giubellina N., and De Kimpe N. Tetrahedron 61 (2005) 2505-2511
21. Iinuma M., Matoba Y., Tanaka T., and Mizuno M. Chem. Pharm. Bull. 34 (1986) 1656-1662
22. Paul E.G., and Wang P.S.C. J. Org. Chem. 44 (1979) 2307-2308
23. Paknikar S.K., Bhattacharjee J., and Nadkarni K.K. J. Indian Inst. Sci. 74 (1994) 277-285
24. Trost B.M., Toste F.D., and Greenman K. J. Am. Chem. Soc. 125 (2003) 4518-4526