Synthesis of acetylated ranunculin diastereoisomers and δ-glucosyloxy-γ-oxo esters from α or β glucosylmethylfurfural

Journal of Carbohydrate Chemistry

Volumn 24, Issue 1, 2005, Pages 55-71

  Cottier, Louis ^a   Descotes, Gérard ^a   Soro, Yaya ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

Furanic compounds; Glycosylation; Photooxygenation; Synthesis

Indexed keywords

EID: 27844606989     PISSN: 07328303     EISSN: 15322327     Source Type: Journal    
DOI: 10.1081/CAR-200049688     Document Type: Article

References (29)

1. Cottier, L.; Descotes, G. 5-Hydroxymethylfurfural, syntheses and chemical transformations. Trends in Heterocycle Chem. 1991, 2, 233-248.
2. Neyret, C.; Cottier, L.; Descotes, G. (Beghin-Say S.A. Fr.) Preparation of 5-hydroxymethylfurfural from saccharides. Fr. 2, 663, 993, Jan. 1992; Chem. Abstr. 1992, 117, 90121b,
3. and New process for the preparation of 5-hydroxymethylfurfural by thermal degradation of sacchardies. Fr. 2, 664, 273, Jan. 1992; Chem. Abstr. 1992, 117, 48323u.
4. Cottier, L.; Descotes, G.; Eymard, L.; Rapp, K. Syntheses of γ-oxo acids or γ-oxo esters by photooxygenation of furanic compounds and reduction under ultrasound: application to the synthesis of 5-amniolevulinic acid hydrochloride. Synthesis 1995 (3), 303-306.
5. Cottier, L.; Descotes, G.; Eymard, L.; Rapp, K. (Südzucker, Ger.) Process for the preparation of N-acylderivatives of 5-aminolevulinic acid and their hydrochlorides. Ger DE 4,228,084, Dec 1993; Chem. Abstr. 1994, 120, 191132y.
6. Li, R.Z.; Ji, X.J. The cytoxicity and action mechanism of ranunculin in vitro. "Yao xue xue bao." 1993, 28, 326-331;
7. Chem. Abstr. 1993, 119, 62606m.
8. Li, R.Z.; Pei, H.P.; Ji, X.J. Antimutagenic activity and metabolic transformation of ranunculin by rat liver microsomes. "Yao xue xue bao." 1993, 28, 481-485;
9. Chem. Abstr. 1993, 119, 240986v.
10. Lichtenthaler, F.W.; Brust, A.; Cuny, E. Sugar derived building block. Part 26. Hydrophilic pyrroles, pyridazines and diazepinones from D-fructose and isomaltulose. Green Chem. 2001, 3 (5), 201-209.
11. Lichtenthaler, F.W. Unsaturated O and N heterocycles from carbohydrates feedstocks. Acc. Chem. Res. 2002, 35 (9), 728-737.
12. Hill, R.; Heyningen, R. Ranunculin: the precursor of the vesicant substance of the buttercup. Biochem. J. 1951, 49, 332-335.
13. Benn, M.H.; Yelland, L.J. Ranunculin. Can. J. Chem. 1968, 46 (5), 729-732.
14. Boll, P.M. Naturally occuring lactones and lactames. I. Absolute configuration of ranunculin, lichesterinic acid and some lactones related to lichesterinic acid. Acta Chem. Scand. 1968, 22 (10), 3245-3250.
15. Cardellach, J.; Estopa, C.; Font, J.; Moreno-Mañas, M.; Ortuno, R.M.; Sacheź-Fernando, F.; Valle, S.; Vilamajo, L. Studies on structurally simple α,β-butenolides - I. New syntheses of racemic γ-hydroxymethyl-α,β-butenolides and derivatives. Tetrahedron 1982, 38 (15), 2377-2394.
16. Camps, P.; Cardellach, J.; Font, J.; Ortuño, R.M.; Pansati, O. Studies on structurally simple αβ-butenolides - II.(-)-(S)-γ- Hydroxymethyl-α,β-butenolides and derivatives from D-ribonolactone efficient synthesis of (-)-ranuculin. Tetrahedron 1982, 38 (15), 2395-2402.
17. Fang, Z.; Zhou, J.; Huang, L. Studies of the total synthesis of (-)-ranunculin. "Yao hsueh hsueh pao." 1989, 24 (3), 182-188;
18. Chem. Abstr. 1990, 112, 77757r.
19. Lichtenthaler, F.W.; Martin, D.; Weber, T.; Schiweck, H. 5-(α-D-Glucosyloxymethyl)furfural: preparation from isomaltulose and exploration of its ensuing chemistry. Liebigs Ann. Chem. 1993 (9), 967-974.
20. Schmidt, R.R.; Michel, J. Facile synthesis of α-and β-O-glycosyl imidates, preparation of glycosides and disaccharides. Angew. Chem., Int. Ed. Engl. 1980, 19 (9), 731-732.
21. Nair, V.; Joseph, J.P. Glycosidation of silyl ethers: a novel synthesis of oligosaccharides and aryl glycosides. Heterocycles 1987, 25, 337-341.
22. Johary, N.S.; Owen, L.N. S-Benzyl derivatives of 2:3-dimercaptopropanol and 1:3 dimercaptopropan-2-ol. J. Chem. Soc. 1955, 1302-1305.
23. Kumar, V.; Amann, A.; Ourisson, G.; Luu, B. Stereospecific syntheses of 7β-and 7α-hydroxycholesterols. Synth. Commun. 1987, 17(11), 1279-1286.
24. Dasgupta, F.; Garegg, P.J. Synthesis of ethyl and phenyl 1-thio-1,2-trans-D-glycopyranosides from the corresponding per-O-acetylated glycopyranoses having a 1,2-trans-configuration using anhydrous ferric chloride as a promoter. Acta Chem. Scand. 1989, 43 (5), 471-475.
25. Misiti, D.; Zappia, G.; Monache, G.D. Selective catalytic hydrogenation of γ-amino α,β-unsaturated esters in the presence of hydrogenable protecting groups. Synthesis 1999 (5), 873-877.
26. Arcadi, A.; Bernochi, E.; Cacchi, S.; Marinelli, F. Palladium catalysed conjugate reduction of α,β-unsaturated carbonyl compounds with potassium formate. Synlett 1991 (1), 27-28.
27. Yu, L.; Chen, D.; Li, J.; Wang, P.G. Preparation, characterization and synthetic uses of lanthanide (III) catalysts supported on ion exchange resins. J. Org. Chem. 1997, 62, 3575-3581.
28. Cottier, L.; Descotes, G.; Lewkowski, J. Synthesis of furan-2,5-dicarbaldehyde by oxidation of 5-siloxymethyl-2-furfural. Synth. Commun. 1994, 24 (7), 939-944.
29. Bernasconi, C.; Cottier, L.; Descotes, G.; Nigay, H.; Parron, J.C.; Wiswiewski, A. Photo-oxygenation of 5-hydroxymethylfurfur-2-al. Bull. Soc. Chim. Fr., 1984 (7,8), II-323-327.