Indium Mediated Allylation in Carbohydrate Chemistry: A Convenient Synthesis of 3-Deoxy-D-arabino-2-heptulosonic acid (DAH) and 3-Deoxy-D-arabino-2-heptulose (Kamusol)

Monatshefte fur Chemie

Volumn 127, Issue 10, 1996, Pages 1045-1050

  Prenner, R H ^a   Schmid, W ^a  

^a INSTITUT FÜR ORGANISCHE CHEMIE   (Austria)

Author keywords

3 deoxy D arabino 2 heptulose (kamusol); 3 deoxy D arabino 2 heptulosonic acid; Indium mediated allylation

Indexed keywords

EID: 0030517039     PISSN: 00269247     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF00807577     Document Type: Article

References (27)

1. (a) Schauer R (1982) Sialic acids. Springer Verlag, Wien
2. (b) Schauer R (1982) Adv Carbohydr Chem Biochem 40: 131
3. Unger FM (1981) Adv Carbohydr Chem Biochem 38: 323
4. Haslam E (1974) The Shikimate Pathway. Butterworth, London
5. Johnson CR, Kozak J (1994) J Org Chem 59: 2910
6. Lopez-Herrera FJ, Sarabia-Garcia F (1994) Tetrahedron Lett 35: 6705
7. Ramage R, MacLeod AM, Rose GW (1991) Tetrahedron 47: 5625
8. Dondoni A, Marra A, Merino P (1994) J Am Chem Soc 116: 3324
9. Reimer LM, Conley DL, Pompliano DL, Frost JW (1986) J Am Chem Soc 108: 8010
10. (a) Garner CC, Herrmann KM (1984) Carbohydr Res 132: 317
11. (b) Sugai T, Shen G-J, Ichikawa Y, Wong C-H (1993) J Am Chem Soc 115: 413
12. Augé C, Delest V (1995) Tetrahedron Asymm 6: 863
13. Horton D, Nickol RG, Varela O (1987) Carbohydr Res 168: 295
14. Banaszek A (1995) Tetrahedron 51: 4231
15. Devianne G, Escudier J-M, Baltas M, Gorrichon L (1995) J Org Chem 60: 7343
16. (a) Binder WH, Prenner WH, Schmid W (1994) Tetrahedron 50: 749
17. (b) Prenner RH, Binder WH, Schmid W (1994) Liebigs Ann Chem 73
18. (a) Chen T-H, Lee M-C (1995) J Org Chem 60: 4228
19. (b) Chen T-H, Li C J (1992) J Chem Soc Chem Commun: 747
20. (a) Gordon DM, Whitesides GM (1993) J Org Chem 58: 7937
21. (b) Gao J, Härter R, Gordon DM, Whitesides GM (1994) J Org Chem 59: 3714
22. Kim E, Gordon DM, Schmid W, Whitesides GM (1993) J Org Chem 58: 5500
23. Cintas P (1995) Synlett: 1087
24. Perlin AS (1962) Methods Carbohydr Chem 1: 64
25. Villieras J, Rambaud M (1987) Org Synth 66: 220
26. Kamal A, Haider Y, Akhtar R, Quereshi AS (1971) Pak J Sci Ind Res 14: 63; (1971) Chem Abstr 75: 126859d
27. Kamal A, Haider Y, Akhtar R, Quereshi AS (1971) Pak J Sci Ind Res 14: 63; (1971) Chem Abstr 75: 126859d