The first synthesis of the ketene dithioacetals from sugar lactones: A convenient access to 3-ulosonic acids

Tetrahedron Letters

Volumn 39, Issue 30, 1998, Pages 5425-5428

  Młynarski, Jacek ^a   Banaszek, Anna ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

Homologation; Ketene; Lactones; Thioacetals

Indexed keywords

ACETAL; CARBOHYDRATE DERIVATIVE; GLYCOSIDE; KETENE DERIVATIVE; LACTONE; SUGAR ACID;

ARTICLE; CHEMICAL REACTION; METHODOLOGY; SYNTHESIS;

EID: 0032560713     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01045-4     Document Type: Article

References (26)

1. [1] Freund E. Ber. Dtsch. Chem. Ges. 1919;52:542-544.
2. [2] Gröbel B-T, Seebach D. Synthesis 1977:357-402.
3. [3] Kolb M. Synthesis 1990:171-190.
4. [4] Carey FA, Court AS. J. Org. Chem. 1972;37:1926-1929.
5. [5] El-Wassimy MTM, Jorgensen KA, Lawesson S-O. J. Chem. Soc., Perkin Trans. 1 1983:2201-2203.
6. [6] Stork G, Zhao K. Tetrahedron Lett. 1989;30:287-290.
7. [7] Corey EJ, Beames DJ. J. Am. Chem. Soc. 1973:95:5829-5831.
8. [8] Marshall JA, Belletire JL. Tetrahedron Lett. 1971:13:871-874.
9. [9] Moss WO, Jones AC, Wisedale R, Mahon MF, Malloy KC, Bradbury RH, Hales NY, Gallagher T J. Chem. Soc. Perkin Trans. 1 1992:2615-2624.
10. [10] Peterson DJ. J. Org. Chem. 1968;33:780-784.
11. [11] Gilman H, Tomasi RA. J. Org. Chem. 1962;27:3647-3650.
12. [12] Nakayawa J, Fujiwara K, Hoshino M. Chem. Lett. 1975:1099.
13. [13] Arai K, Oki M. Tetrahedron Lett. 1975;30:2183-2186.
14. [14] Mikołajczyk M, Grzejszczak S, Zatorski A, Młotkowska B. Tetrahedron Lett. 1976;31:2731-2734.
15. [15] Mink D, Deslongchamps G. Synlett 1996:875-876.
16. [16] Mikołajczyk M, Graczyk PP. Wieczorek MW. J. Org. Chem. 1994;59:1672-1693.
17. [17] Still WC, Gennari C. Tetrahedron Lett. 1983;24:4405-4408.
18. [18] Rollin P, Sinaÿ P. Carbohydr. Res. 1981;98:139-142.
19. [19] Unger FM. Adv. Carbohydr. Chem. Biochem. 1981;38:323-388.
20. [20] Schauer R. Adv. Carbohydr. Chem. Biochem. 1982;40:131-234.
21. [21] Corey EJ, Erickson BW. J. Org. Chem. 1971;36:3553-3560.
22. [22] Harville R, Reed SF Jr. J. Org. Chem. 1968;33:3976-3977.
23. [23] Crich D, Ritchie TJ. J. Chem. Soc. Perkin Trans. 1 1990:945-955.
24. [24] Banaszek A. Tetrahedron 1995;51:4231-4238.
25. [25] Młynarski, J, Banaszek A. Carbohydrate Lett. 1997;2:409-414.
26. [26] Młynarski J, Banaszek A. Carbohydr. Res. 1996;295:69-75.