Asymmetric syntheses of (-)-methyl shikimate and (-)-5a-carba-β-d-gulopyranose from d-arabinose via Mukaiyama-type intramolecular aldolization

Tetrahedron Asymmetry

Volumn 20, Issue 1, 2009, Pages 78-83

  Liu, Shi Ling ^a   Shi, Xiao Xin ^a   Xu, Yu Lan ^a   Xu, Wei ^a   Dong, Jing ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

5A CARBA BETA DEXTRO GULOPYRANOSE [ 5 HYDROXYMETHYLCYCLO HEXANE 1,2,3,4 TETROL]; ARABINOSE DERIVATIVE; METHYLSHIKIMATE; SHIKIMIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; MUKAIYAMA REACTION; OLEFINATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; THIN LAYER CHROMATOGRAPHY;

EID: 61349176994     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.12.028     Document Type: Article

References (58)

1. Shibasaki M., and Kanai M. Eur. J. Org. Chem. (2008) 1839
2. Farina V., and Brown J.D. Angew. Chem., Int. Ed. 45 (2006) 7330
3. Zutter U., Iding H., Spurr P., and Wirz B. J. Org. Chem. 73 (2008) 4895
4. Kim C.U., Lew W., Williams M.A., Liu H., Zhang L., Swaminathan S., Bischofberger N., Chen M.S., Mendel D.B., Tai C.Y., Laver W.G., and Stevens R.C. J. Am Chem. Soc. 119 (1997) 681
5. Rohloff J.C., Kent K.M., Postich M.J., Becker M.W., Chapman H.H., Kelly D.E., Lew W., Louie M.S., McGee L.R., Prisbe E.J., Schultze L.M., Yu R.H., and Zhang L. J. Org. Chem. 63 (1998) 4545
6. Federspiel M., Fischer R., Hennig M., Mair H.-J., Oberhauser T., Rimmler G., Albiez T., Bruhin J., Estermann H., Gandert C., Gockel V., Gotzo S., Hoffmann U., Huber G., Janatsch G., Lauper S., Rockel-Stabler O., Trussardi R., and Zwahlen A.G. Org. Process Res. Dev. 3 (1999) 266
7. Eykman J.F. Recl. Trav. Chim. Pays-Bas 4 (1885) 32
8. McCrindle R., Overton K.H., and Raphael R.A. J. Chem. Soc. (1960) 1560
9. Smissman E.E., Suh J.T., Oxman M., and Daniels R. J. Am. Chem. Soc. 81 (1959) 2909
10. Jiang S., and Singh G. Tetrahedron 54 (1998) 4697
11. Koreeda M., and Ciufolini M.A. J. Am. Chem. Soc. 104 (1982) 2308
12. Koreeda M., Teng K., and Murata T. Tetrahedron Lett. 31 (1990) 5997
13. Koreeda M., Jung K.-Y., and Ichita J.-J. J. Chem. Soc., Perkin Trans. 1 (1989) 2129
14. Ogawa S., Aoki Y., and Takagaki T. Carbohydr. Res. 164 (1987) 499
15. Barlett P.A., and McQuaid L.A. J. Am. Chem. Soc. 106 (1984) 7854
16. Choy W., and Reed L.A. J. Org. Chem. 48 (1983) 1137
17. Masamune S., and Reed L.A. J. Org. Chem. 48 (1983) 4441
18. Takahashi T., and Namiki T. Chem. Pharm. Bull. 36 (1988) 3213
19. Pawlak J.L., and Berchtold G.A. J. Org. Chem. 52 (1987) 1765
20. Kamikubo T., and Ogasawara K. Chem. Lett. (1996) 987-988
21. Hiroya K., and Ogasawara K. Chem. Commun. (1998) 2033
22. Ogasawara K., and Yoshida N. Org. Lett. 2 (2000) 1461
23. Coblens K.E., Muralidharan V.B., and Ganem B. J. Org. Chem. 47 (1982) 5041
24. Ikota N., and Ganem B. J. Am. Chem. Soc. 100 (1978) 351
25. Birch A.J., Kelly L.F., and Weerasuria D.V. J. Org. Chem. 53 (1988) 278
26. Johnson C.R., Adams J.P., and Collins M.A. J. Chem. Soc., Perkin Trans. 1 (1993) 1
27. Johnson C.R., Ple P.A., and Adams J.P. J. Chem. Soc., Chem. Commun. (1991) 1006
28. Takeuchi M., Taniguchi L., and Ogasawara K. Synthesis (2000) 1375
29. Dangschat T., and Fischer M. Biochim. Biophys. Acta 4 (1950) 199
30. Grewe R., Buttner H., and Burmeister G. Angew. Chem. 69 (1957) 61
31. Shinada T., Yoshida Y., and Ohfune Y. Tetrahedron Lett. 39 (1998) 6027
32. Alves C., Barros M.T., Maycock C.D., et al. Tetrahedron 55 (1999) 8443
33. Bestmann H.J., and Heid H.A. Angew. Chem., Int. Ed. Engl. 10 (1971) 336
34. Suami T., Tadano K., Ueno Y., and Iimura Y. Chem Lett. (1985) 37
35. Tadano K., Ueno Y., Iimura Y., and Suami T. J. Carbohydr. Chem. 6 (1987) 245
36. Fleet G.W.J., Shing T.K.M., and Warr S.M. J. Chem. Soc., Perkin Trans. 1 (1984) 905
37. Mirza S., and Vasella A. Helv. Chim. Acta 67 (1984) 1562
38. Mirza S., and Harvey J. Tetrahedron Lett. 32 (1991) 4111
39. Jiang S., Mekki B., and Singh G. Tetrahedron Lett. 35 (1994) 5505
40. Inch T.D. Tetrahedron 40 (1984) 3161
41. Mukaiyama T., Narasaka K., and Banno K. Chem. Lett. (1973) 1011
42. Mukaiyama T., Banno K., and Narasaka K. J. Am. Chem. Soc. 96 (1974) 7503
43. Mukaiyama T. Org. React. 28 (1982) 203
44. Maryanoff B.E., and Reitz A.B. Chem. Rev. 89 (1989) 863
45. Lyga J.W. Org. Prep. Proced. Int. 24 (1992) 73
46. Corey E.J., and Suggs J.W. Tetrahedron Lett. 16 (1975) 2647
47. Dess D.B., and Martin J.C. J. Am. Chem. Soc. 113 (1991) 7277
48. Rassu G., Auzzas L., Pinna L., Battistini L., Zanardi F., Marzocchi L., Acquotti D., and Casiraghi G. J. Org. Chem. 65 (2000) 6307
49. Rassu G., Auzzas L., Pinna L., Zambrano V., Battistini L., Zanardi F., Marzocchi L., Acquotti D., and Casiraghi G. J. Org. Chem. 66 (2001) 8070
50. Suami T. Pure Appl. Chem. 59 (1987) 1509
51. Agrofoglio L., Suhas E., Farese A., Condom R., Challand S.R., Earl R.A., and Guedj R. Tetrahedron 50 (1994) 10611
52. Marquez V.E., and Lim M. Med. Res. Rev. 6 (1986) 1
53. Suami T. Top. Curr. Chem. 154 (1990) 257
54. Asano N., Nash R.J., Molyneux R.J., et al. Tetrahedron: Asymmetry 11 (2000) 1645
55. Heightman T.D., and Vasella A.T. Angew. Chem., Int. Ed. 38 (1999) 750
56. Berecibar A., Grandjean C., and Siriwardena A. Chem. Rev. 99 (1999) 779
57. Tanaka K.S.E., Winters G.C., Batchelor R.J., et al. J. Am. Chem. Soc. 123 (2001) 998
58. Zanardi F., Battistini L., Marzocchi L., Acquotti D., Rassu G., Pinna L., Auzzas L., Zambrano V., and Casiraghi G. Eur. J. Org. Chem. (2002) 1956