Concise synthesis of 3-deoxy-D-manno-oct-2-ulosonic acid (KDO) as a protected form based on a new transformation of α,β-unsaturated ester to α-oxocarboxylic acid ester via diol cyclic sulfite

Tetrahedron Letters

Volumn 45, Issue 23, 2004, Pages 4545-4548

  Kuboki, Atsuhito ^a   Tajimi, Toshihiro ^a   Tokuda, Yoshihide ^b   Kato, Dai Ichiro ^b   Sugai, Takeshi ^b   Ohira, Susumu ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

^b KEIO UNIVERSITY   (Japan)

Author keywords

elimination; Cyclic sulfite; KDO

Indexed keywords

3 DEOXY MANNO OCTULOSONIC ACID; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; ETHER DERIVATIVE; FURAN DERIVATIVE; MANNOSE; SILANE DERIVATIVE; SULFITE;

ARTICLE; BIOTRANSFORMATION; DEPROTECTION REACTION; DRUG SYNTHESIS; ELIMINATION REACTION; QUANTUM YIELD; REACTION ANALYSIS;

EID: 2342513331     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.04.016     Document Type: Article

References (28)

1. Alexander C., Reitschel E.T. Biospektrum. 4:1999;275-282
2. Unger F.M. Adv. Carbohydr. Chem. Biochem. 38:1981;323-388. and references cited therein
3. For recent examples of syntheses from carbohydrates, see: Hekking K.F.W., van Delft F.L., Rutjes P.J.T. Tetrahedron. 59:2003;6751-6758. and references cited therein
4. Wardrop D.J., Zhang W. Tetrahedron Lett. 43:2002;5389-5391
5. Li L.-S., Wu Y.-L. Tetrahedron Lett. 43:2002;2427-2430
6. Sarabia F., López-Herrera J. Tetrahedron Lett. 42:2001;8801-8804
7. Kumaran G., Mootoo D.R. Tetrahedron Lett. 42:2001;3783-3785
8. Reiner M., Schmidt R.R. Tetrahedron: Asymmetry. 11:2000;319-335
9. van der Klein P.A.M., Boons G.J.P.H., Veeneman G.H., van der Marel G.A., van Boom J.H. Tetrahedron Lett. 30:1989;5477-5480
10. Imoto M., Kusumoto S., Shiba T. Tetrahedron Lett. 28:1987;6235-6239
11. For de novo syntheses, see: Barco A., Bassetti L., Benetti S., Bertolasi V., De Risi C., Marchetti P., Pollini G.P. Tetrahedron. 58:2002;8553-8558
12. Burke S.D., Sametz G.M. Org. Lett. 1:1999;71-74
13. Schlessinger R.H., Pettus L.H. J. Org. Chem. 63:1998;9089-9094
14. Hu Y.-J., Huang X.-D., Yao Z.-J., Wu Y.-L. J. Org. Chem. 63:1998;2456-2461
15. Lubineau A., Augé J., Lubin N. Tetrahedron. 49:1993;4639-4650
16. Martin S.F., Zinke P.W. J. Org. Chem. 56:1991;6600-6606
17. Dondoni A., Merino P. J. Org. Chem. 56:1991;5294-5301
18. Smith D.B., Wang Z., Schreiber S.L. Tetrahedron. 46:1990;4793-4808
19. Danishefsky S.J., DeNinno M.P., Chen S.-H. J. Am. Chem. Soc. 110:1988;3929-3940
20. Crestia D., Guerard C., Bolte J., Demuynck C. J. Mol. Cat. B: Enz. 11:2001;207-212
21. Kragl U., Gödde A., Wandrey C., Lubin N., Augé C. J. Chem. Soc., Perkin Trans. 1. 1994;119-124
22. Sugai T., Shen G.-J., Ichikawa Y., Wong C.-H. J. Am. Chem. Soc. 115:1993;413-421
23. Bednarski M.D., Crans D.C., DiCosimo R., Simon E.S., Stein P.D., Whitesides G.M. Tetrahedron Lett. 29:1988;427-430
24. Gourlain T., Wadouachi A., Beaupere D. Tetrahedron Lett. 41:2000;659-662
25. Collins P.M., Overend W.G., Shing T.K.M. J. Chem. Soc., Chem. Commun. 1981;1139-1140
26. The self-condensation could be avoided by lowering concentration of the substrate (12 mM) and by trapping of enolate with the excessive base (3.3 equiv). The reverse addition of substrate to the base was also efficient. As a result, the yield of 8a increased to 82%. However, 2 could not be obtained from 6 by the improved procedure
27. +. Found: 347.1682
28. +. Found: 483.2400