A new and convenient one-step synthesis of the natural 3-deoxyanthocyanidins apigeninidin and luteolinidin chlorides from 2,4,6-triacetoxybenzaldehyde

Synthesis

Volumn , Issue 12, 2003, Pages 1878-1880

  Mas, Thierry ^a,b  

^a UNIVERSITÉ DE BORDEAUX   (France)

^b UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

Heterocycles; Natural products; Polycycle; Sphenols; Total synthesis

Indexed keywords

ALDEHYDES; CONDENSATION; KETONES;

COMMERCIAL REAGENTS;

SYNTHESIS (CHEMICAL);

2,4,6 TRIACETOXYBENZALDEHYDE; 3 DEOXYANTHOCYANIDIN DERIVATIVE; 5,7 DIHYDROXYFLAVYLIUM CHLORIDE; ANTHOCYANIN; APIGENINIDIN CHLORIDE; BENZALDEHYDE DERIVATIVE; HETEROCYCLIC COMPOUND; LUTEOLINIDIN CHLORIDE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; SYNTHESIS; TECHNIQUE;

EID: 0141519428     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40982     Document Type: Article

References (21)

1. (a) Strack, D.; Wray, V. In The Flavonoids, Advances in Research since 1986; Harborne, J. B., Ed.; Chapman and Hall: London, 1994, 1-22.
2. (b) Brouillard, R.; Dangles, O. In The Flavonoids, Advances in Research since 1986; Harborne, J. B., Ed.; Chapman and Hall: London, 1994, 565-588.
3. (a) Mazza, G.; Miniati, E. In Anthocyanins in Fruits, Vegetables and Grains; CRC Press: Boca Raton, 1993, 225-248.
4. (b) Timberlake, C. F.; Bridle, P. In Anthocyanins as Food Colors; Markakis, P., Ed.; Academic Press: New York, 1982, 126-162.
5. (a) Sweeny, J. G.; Iacobucci, G. A. J. Agric. Food Chem. 1983, 31, 531.
6. (b) Iacobucci, G. A.; Sweeny, J. G. CocaCola Co, Eur. Patent Applic. 24731, 1979; Chem. Abstr. 1981, 95: 5399h.
7. Darmenton, P.; Philippe, M. L'Oreal S.A. FR 2757383, 1996; Chem. Abstr. 1998, 129, 140458n.
8. Mas, T.; Susperregui, J.; Berké, B.; Chèze, C.; Moreau, S. ; Nuhrich, A.; Vercauteren, J. Phytochemistry 2000, 53, 679.
9. Mas, T.; Susperregui, J.; Moreau, S.; Vercauteren, J. Color of Wine: A New Therapeutic Tool? In Oenologic Actualities 1999; 6th International Oenology Symposium: Bordeaux, 1999.
10. Vergé, S.; Mas, T.; Nay, B.; Arnaudinaud, V.; Soulet, S.; Richard, T.; Castagnino, C.; Delaunay, J. C.; Chèze, C.; Monti, J. P.; Vercauteren, J. Scientific Registers of the European Institute 2000, 9.
11. Thuong, N. T.; Hélne, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 666.
12. (a) Robinson, G. M.; Robinson, R.; Todd, A. R. J. Chem. Soc. 1934, 809.
13. (b) Leon, A.; Robinson, R. J. Chem. Soc. 1931, 2732.
14. (c) Pratt, D. D.; Robinson, R. J. Chem. Soc. 1925, 1128.
15. Sweeny, J. G.; Iacobucci, G. A. Tetrahedron 1981, 37, 1481.
16. Sweeny, J. G.; Iacobucci, G. A. Tetrahedron 1977, 33, 2927.
17. (a) Pratt, D. D.; Robinson, R. J. Chem. Soc. 1923, 745.
18. (b) Perkin, W. H.; Robinson, R.; Turner, M. R. J. Chem. Soc 1908, 93, 1085.
19. (c) Perkin, W. H.; Robinson, R. Proc. Chem. Soc. 1907, 19, 149
20. Dean, F. M.; Patamapongse, C. J. Chem. Soc., Perkin Trans. 1 1974, 8, 952.
21. El Hajji, H.; Dangles, O.; Statoua, A.; Brouillard, R. Polyphénols Actualités 1996, 15, 7.