Expedient conversion of d-glucose into 1,5-anhydro-d-fructose and into single stereogenic-center dihydropyranones, suitable six-carbon scaffolds for concise syntheses of the soft-coral constituents (-)-bissetone and (-)-palythazine

Tetrahedron Asymmetry

Volumn 19, Issue 3, 2008, Pages 358-373

  Brehm, Manfred ^a   Göckel, Volker H ^a   Jarglis, Pan ^a   Lichtenthaler, Frieder W ^a  

^a DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1,5 ANHYDRO DEXTRO FRUCTOSE; BISSETONE; DIHYDROPYRANONE DERIVATIVE; FRUCTOSE; GLUCOSE; HYDROXYGLUCAL ESTER DERIVATIVE; PALYTHAZINE; PYRONE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ADDITION REACTION; AMINOLYSIS; ARTICLE; CHEMICAL STRUCTURE; ENZYMATIC DEGRADATION; LOW TEMPERATURE; PRIORITY JOURNAL;

EID: 39149131680     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.01.019     Document Type: Article

References (55)

1. Lergenmüller M., and Lichtenthaler F.W. Carbohydr. Res. 342 (2007) 2132-2137
2. Deffieux G., Baute R., Baute M.-A., Atfani M., and Carpy A. Phytochemistry 26 (1987) 1391-1393
3. Andersen S.M., Lundt I., Marcussen J., and Yu S. Carbohydr. Res. 337 (2002) 873-890
4. Lichtenthaler F.W., El Ashry E.S.H., and Göckel V.H. Tetrahedron Lett. 21 (1980) 1429-1432
5. Göckel, V. H. Ph.D. Dissertation, Technische Hochschule Darmstadt, 1984, as cited in Ref. 3.
6. Nakamura, T.; Takahashi, A.; Kato, K. (Nippon Kagaku Co.) Jap. Pat. 63-072696, 1988, appl. 1986; Chem. Abstr. 1988, 510835.
7. Dekany G., Lundt I., Niedermair F., Bichler S., Spreitz J., Sprenger F.K., and Stütz A.E. Carbohydr. Res. 342 (2007) 1249-1253
8. Overall yields calculated on the basis of literature data for the first two steps, that is, 75% (Bell, D. H., J. Chem. Soc. 1947, 1461-1463) and 81% (Barnett, J. E. G.; Atkins, G. R. S. Carbohydr. Res. 1972, 25, 511-515).
9. Baute A., Baute R., and Deffieux G. Phytochemistry 27 (1988) 3401-3403
10. Taguchi T., Haruna M., and Okuda J. J. Biotechnol. Appl. Biochem. 18 (1993) 275-283
11. Yu S., Kenne M., and Pedersén M. Biochim. Biophys. Acta 1244 (1995) 1-9
12. Freimund S., Huwig A., Giffhorn F., and Köpper S. Chem. Eur. J. 4 (1998) 2442-2455
13. Fujisue M., Yoshinaga K., Muroya K., Abe J., and Hizukuri S. J. Appl. Glycosci. 46 (1999) 439-444
14. Yamaji K., Pada Sarker K., Maruyama I., and Hizukuri S. Planta Med. 68 (2002) 16-19
15. See extensive patent literature cited in Ref. 7a.
16. Ahrén B., Holst J.J., and Yu S. Eur. J. Pharmacol. 397 (2000) 219-225
17. 3,12b been designated as a chiral building block-a misleading term since a compound with a carbonyl function and three OH groups on a six-carbon skeleton is a monosaccharide, like glucose or fructose.
18. Maier P., Andersen S.M., and Lundt I. Synthesis (2006) 827-830
19. Jarglis P., and Lichtenthaler F.W. Angew. Chem. 94 (1982) 140-141
20. Jarglis P., and Lichtenthaler F.W. Angew. Chem., Int. Ed. Engl. 21 (1982) 141-142
21. Brehm M., Dauben W.G., Köhler P., and Lichtenthaler F.W. Angew. Chem. 29 (1987) 1318-1319
22. Brehm M., Dauben W.G., Köhler P., and Lichtenthaler F.W. Angew. Chem., Int. Ed. Engl. 26 (1987) 1271-1273
23. Maurer K., and Mahn H. Ber. Dtsch. Chem. Ges. 60 (1927) 1316-1320
24. Maurer K. Ber. Dtsch. Chem. Ges. 62 (1929) 332-338
25. Maurer K., and Petsch W. Ber. Dtsch. Chem. Ges. 66 (1933) 995-1000
26. Lemieux R.U. Methods Carbohydr. Chem. 2 (1963) 221-222
27. Fletcher Jr. H.G. Methods Carbohydr. Chem. 2 (1963) 226-228
28. Blair M.G. Methods Carbohydr. Chem. 2 (1963) 411-414
29. Ferrier R.J., and Sankey G.H. J. Chem. Soc. C (1966) 2339-2345
30. Ferrier R.J. Methods Carbohydr. Chem. 6 (1972) 307-311
31. Lichtenthaler F.W., and Schneider-Adams T. J. Org. Chem. 59 (1994) 6728-6734
32. For reviews, see:. Kaji E., and Lichtenthaler F.W. Trends Glycosci. Glycotechnol. 5 (1993) 121-142
33. Gridley J.J., and Osborn H.M.I. J. Chem. Soc., Perkin Trans. 1 (2000) 1471-1491
34. Pozsgay V. Carbohydrates. In: Ernst B., Hart G., and Sinaÿ P. (Eds). Chemistry and Biology, Part I (2000), Wiley-VCH, Weinheim 332-336
35. For recent applications towards β-d-mannosides, see:. Nitz M., and Bundles D.R. J. Org. Chem. 66 (2001) 8411-8423
36. Lichtenthaler F.W., Lergenmüller M., and Schwidetzky S. Eur. J. Org. Chem. (2003) 3094-3103
37. Lichtenthaler F.W., Rönninger S., and Jarglis P. Liebigs Ann. Chem. (1989) 1153-1161
38. For pertinent reviews, see:. Lichtenthaler F.W. Pure Appl. Chem. 50 (1978) 1343-1362
39. Lichtenthaler F.W. In: Scheffold R. (Ed). Modern Synthetic Methods (1992), VCH, Weinheim/New York 273-376
40. Lichtenthaler, F. W. In Carbohydrate Synthons in Natural Product Chemistry, Witczak, Z. J., Tatsuta, K., Eds.; ACS Symp. Series Nr. 841; Washington, DC, 2003; pp 47-83.
41. Lichtenthaler F.W., Cuny E., and Sakanaka O. Angew. Chem. 117 (2005) 5024-5028
42. Lichtenthaler F.W., Cuny E., and Sakanaka O. Angew. Chem., Int. Ed. 44 (2005) 4944-4948
43. Cuny E., and Lichtenthaler F.W. Tetrahedron: Asymmetry 17 (2006) 1020-1024
44. For a preliminary report on the hydroxylaminolysis of enol esters, see:. Lichtenthaler F.W., and Jarglis P. Tetrahedron Lett. 21 (1980) 1425-1428
45. 24b.{A figure is presented}
46. Bergmann M., and Zervas L. Ber. Dtsch. Chem. Ges. 64 (1931) 1434-1438
47. Corbett W.M. J. Chem. Soc. C (1959) 3213-3216
48. Cardellina J.H., Hendrickson R.L., Manfredi K.P., Strobel S.A., and Clardy J. Tetrahedron Lett. 28 (1987) 727-730
49. Uemura D., Toya Y., Watanabe I., and Hirata Y. Chem. Lett. (1979) 1481-1482
50. Andersen S.M., Lundt I., and Marcussen J. J. Carbohydr. Chem. 19 (2000) 717-725
51. Conditions adapted from those used for the effective deoximation of glycoside-2-ulose oximes by. Lemieux R.U., Earl R.A., James K., and Nagabushan T.L. Can. J. Chem. 51 (1973) 19-27
52. Freimund S., and Köpper S. Carbohydr. Res. 308 (1998) 195-200
53. Andersen S.M., Lundt I., Marcussen J., Søtofte L., and Yu S. J. Carbohydr. Chem. 17 (1998) 1027-1035
54. Sheldrick, G. M. shelxs-97: Program for Crystal Structure Solution, Göttingen, 1997.
55. Sheldrick, G. M. shelxs-97: Program for Crystal Structure Refinement, Göttingen, 1997.