Syntheses of D- and L-mannose, gulose, and talose via diastereoselective and enantioselective dihydroxylation reactions

Journal of Organic Chemistry

Volumn 64, Issue 9, 1999, Pages 2982-2983

  Harris, Joel M ^a   Keranen, Mark D ^a   O'Doherty, George A ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GULOSE; MANNOSE; OLIGOSACCHARIDE; TALOSE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; ENANTIOMER; HYDROLYSIS; HYDROXYLATION; STEREOISOMERISM; SYNTHESIS;

EID: 0033617277     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990410+     Document Type: Article

References (36)

1. For a good review: Zamoiski, A.; Banaszek, A.; Grynkiewicz, G. Adv. Carbohydr. Chem. Biochem. 1982, 40, 1.
2. Sharpless, K. B.; Masamune, S. Science 1983, 220, 949.
3. For a review, see: (a) Danishefsky, S. J. Chemtracts 1989, 273. For improved catalysis, see: (b) Schaus, S. E.; Branalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403-405.
4. For a review, see: (a) Danishefsky, S. J. Chemtracts 1989, 273. For improved catalysis, see: (b) Schaus, S. E.; Branalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403-405.
5. (a) Johnson, C. R.; Golebiowski, A.; Steensma, D. H.; Scialdone, M. A. J. Org. Chem. 1993, 58, 7185-7194.
6. (b) Hudlicky, T.; Pitzer, K. K.; Stabile, M. R.; Thorpe, A. J.; Whited, G. M. J. Org. Chem. 1996, 61, 4151-4153.
7. Henderson, I.; Sharpless, K. B.; Wong, C.-H. J. Am. Chem. Soc. 1994, 116, 558-561.
8. Recently Wong has developed a route to a mixture of glucose and fructose using an enzymatic process: Gijsen, H. J. M.; Qiao, L.; Fitz, W.; Wong, C.-H. Chem. Rev. 1996, 96, 443-73.
9. Riccio, R.; Kinnel, R. B.; Bifulco, G.; Scheur, P. J. Tetrahedron Lett. 1996, 37, 1979.
10. For a recent total synthesis of bleomycin, see: (a) Boger, D. L.; Honda, T. J. Am. Chem. Soc. 1994, 116, 5647-5656. (b) Boger, D. L.; Honda, T.; Menezes, R. F.; Colletti, S. L. J. Am. Chem. Soc. 1994, 116, 5631-5646. (c) Boger, D. L.; Teramoto, S.; Zhou, J. C. J. Am. Chem. Soc. 1995, 117, 7344- 7356.
11. For a recent total synthesis of bleomycin, see: (a) Boger, D. L.; Honda, T. J. Am. Chem. Soc. 1994, 116, 5647-5656. (b) Boger, D. L.; Honda, T.; Menezes, R. F.; Colletti, S. L. J. Am. Chem. Soc. 1994, 116, 5631-5646. (c) Boger, D. L.; Teramoto, S.; Zhou, J. C. J. Am. Chem. Soc. 1995, 117, 7344- 7356.
12. For a recent total synthesis of bleomycin, see: (a) Boger, D. L.; Honda, T. J. Am. Chem. Soc. 1994, 116, 5647-5656. (b) Boger, D. L.; Honda, T.; Menezes, R. F.; Colletti, S. L. J. Am. Chem. Soc. 1994, 116, 5631-5646. (c) Boger, D. L.; Teramoto, S.; Zhou, J. C. J. Am. Chem. Soc. 1995, 117, 7344-7356.
13. According to the Aldrich catalog, on a per gram basis D-mannose cost 35 times more than furfural and for L-mannose the cost ratio is 4000.
14. Furfural is commercially produced by Great Lakes Chemical. For a convenient laboratory procedure, see: Adams, R.; Voorhees, V. Organic Syntheses; Wiley: New York, 1921; Collect. Vol. I, p 280.
15. (a) Achmatowicz, O.; Bielski, R. Carbohydr. Res. 1977, 55, 165.
16. (b) Grapsas, I.; K.; Couladouros, E. A.; Georgiadis, M. P. Pol. J. Chem. 1990, 64, 823.
17. Ogasawara has previously demonstrated the asymmetric dihydroxy-lation of vinylfuran and applied it toward the synthesis of D- and L-levoglucosenone: (a) Taniguchi, T.; Nakamura, K.; Ogasawara, K. Synlett 1996, 971. (b) Taniguchi, T.; Ohnishi, H.; Ogasawara, K. Chem. Commun. 1996, 1477-1478.
18. Ogasawara has previously demonstrated the asymmetric dihydroxy- lation of vinylfuran and applied it toward the synthesis of D- and L- levoglucosenone: (a) Taniguchi, T.; Nakamura, K.; Ogasawara, K. Synlett 1996, 971. (b) Taniguchi, T.; Ohnishi, H.; Ogasawara, K. Chem. Commun. 1996, 1477-1478.
19. For a good review, see: Hudlicky, T.; Entwistle, D. A.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195.
20. This in situ use of vinylfuran allows for much higher yields of diol 7. Wittig technology provides vinylfuran in yields on the order of 10%. Previous practical approaches to vinylfuran involve a four-step sequence from furfural that involves a stoichiometric Cu-promoted decarboxylation of 3-furylpropanoic acid, see: Schmidt, U.; Werner, J. Synthesis 1986, 986.
21. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
22. 2O; see ref 12a.
23. The (R) diol 7 has been prepared on a half mole scale with no reduction of enantioselectivity. Similarly the (S) diol 7 has been prepared on a quarter mole scale.
24. (a) Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1975, 38, 2143.
25. (b) Yamaguchi, S.; Yasuhara, F.; Kabuto, K. T. Tetrahedron 1976, 32, 1363.
26. Georgiadis, M. P.; Couladoures, E. A. J. Org. Chem. 1986, 51, 2725 and ref 11b.
27. 3N gave a 1:1 mixture. Achmatowicz has previously shown that molecules related to 6a gave a 1:1 mixture of methoxy anomers with MeOH/ acid; see ref 11a.
28. Luche, J.-L. J. Am. Chem. Soc. 1978, 110, 2226.
29. Mosher ester analysis of 7a showed that recrystallized enone 6b had significantly increased enantioexcess (>96% ee).
30. For a review of diastereoselection in the osmium-catalyzed dihydroxylation reaction, see: Cha, J. K.; Kim, N.-S. Chem. Rev. 1995, 95, 1761.
31. 1H NMR.
32. (a) Martin, S. P.; Dodge, J. A.Tetrahedron Lett. 1991, 32, 3017.
33. (b) Grynkiewicz, G. Pol. J. Chem. 1979, 53, 2501.
34. (c) Mitsunobu, O. Compr. Org. Synth. 1991, 6, 1.
35. For a recent eight-step synthesis of gulose from L-xylose, see: Dondoni, A.; Marra, A.; Massi, A. J. Org. Chem. 1997, 62, 6261. Dondoni appraises L-gulose at $2000/g.
36. Less than 5% of the gulose isomer was formed. These conditions were chosen for the hydroxy-directed delivery of a ris diol. See: Donohoe, T. J.; Moore, P. R.; Waring, M. J.; Newcombe, N. J. Tetrahedron Lett. 1997, 38, 5027.