A concise route to (-)-shikimic acid and (-)-5-epi-shikimic acid, and their enantiomers via Barbier reaction and ring-closing metathesis

Tetrahedron Letters

Volumn 50, Issue 50, 2009, Pages 6951-6954

  Kancharla, Pavan K ^a   Doddi, Venkata Ramana ^a   Kokatla, Hariprasad ^a   Vankar, Yashwant D ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

Barbier reaction; Carbasugars; epi Shikimic acid; Ring closing metathesis; Shikimic acid

Indexed keywords

SHIKIMIC ACID DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS;

EID: 71049171247     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.09.111     Document Type: Article

References (42)

1. Eykman J.F. Recl. Tray. Chim. Pays-Bas 4 (1885) 32
2. Kishore G.M., and Shah D.M. Annu. Rev. Biochem. 57 (1988) 627
3. U.S. Environmental Protection Agency. Technical Factsheet on: GLYPHOSATE, 2006.
4. Sikorski J. Acc. Chem. Res. 30 (1997) 2
5. Roberts F., Roberts C.W., Johnson J.J., Kyle D.E., Krell T., Coggins J.R., Coombs G.H., Milhous W.K., Tzipori S., Ferguson D.J.P., Chakrabarti D., and McLeod R. Nature 393 (1998) 801
6. Johansson L., and Liden G. J. Biotechnol. 126 (2006) 528
7. Kim C.U., Liu W., Williams M.A., Liu H., Zhang L., Swaminathan S., Bischofberger N., Chen M.S., Mendel D.B., Tai C.Y., Laver G., and Stevens R.C. J. Am. Chem. Soc. 119 (1997) 681
8. 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
9. Nie L.-D., Shi X.-X., Ko K.H., and Lu W.-D. J. Org. Chem. 74 (2009) 3970
10. Trifonov V., Khiabanian H., Greenbaum B., and Rabadan R. Eurosurveillance 4 (2009) 17
11. Jiang S., Singh G., Boam D.J., and Coggins J.R. Tetrahedron: Asymmetry 10 (1999) 4087
12. Brettle R., Cross R., Frederickson M., Haslam E., MacBeath F.S., and Davies G.M. Tetrahedron 52 (1996) 10547
13. Adams H., Bailey N.A., Brettle R., Cross R., Frederickson M., Haslam E., MacBeath F.S., and Davies G.M. Tetrahedron 52 (1996) 8565
14. Armesto N., Ferrero M., Fernández S., and Gotor V. Tetrahedron Lett. 41 (2000) 8759 and references cited therein
15. Posner G.H., and Wettlaufer D.G. J. Am. Chem. Soc. 108 (1986) 7373
16. Pornpakakul S., Pritchard R.G., and Stoodley R.J. Tetrahedron Lett. 41 (2000) 2691
17. Snyder C.D., and Rapoport H. J. Am. Chem. Soc. 95 (1973) 7821
18. Usami Y., Takaoka I., Ichikawa H., Horibe Y., Tomiyama S., Ohtsuka M., Imanishi Y., and Arimoto M. J. Org. Chem. 72 (2007) 6127
19. Kamiya D., Uchiata Y., Ichikawa E., Kato K., and Umezawa K. Bioorg. Med. Chem. Lett. 15 (2005) 1111
20. Bohm B.A. Chem. Rev. 65 (1965) 435
21. Jiang S., and Singh G. Tetrahedron 54 (1998) 4697
22. Bestmann H.J., and Held H.A. Angew. Chem., Int. Ed. Engl. 10 (1971) 336
23. Jiang S., Mekki B., Sing G., and Wightman R.H. Tetrahedron Lett. 35 (1994) 5505
24. Jiang S., Mekki B., Singh G., and Wightman R.H. J. Chem. Soc., Perkin Trans. 1 (1997) 1805
25. Mirza S., and Vasella A. Helv. Chim. Acta 67 (1984) 1562
26. Smith III A.B., Han Q., Breslin P.A.S., and Beauchamp G.K. Org. Lett. 7 (2005) 5075
27. Hanessian S., Beaulieu P., and Dube D. Tetrahedron Lett. 27 (1986) 5071
28. Lesuisse D., and Berchtold G.A. J. Org. Chem. 50 (1985) 888
29. Doddi V.R., Kumar A., and Vankar Y.D. Tetrahedron 64 (2008) 9117
30. Doddi V.R., Kancharla P.K., Reddy Y.S., Kumar A., and Vankar Y.D. Carbohydr. Res. 344 (2009) 606
31. Kumar A., Rawal G.K., and Vankar Y.D. Tetrahedron 64 (2008) 2379
32. Ramana D.V., and Vankar Y.D. Eur. J. Org. Chem. (2007) 5583
33. Reddy B.G., and Vankar Y.D. Angew. Chem., Int. Ed. 44 (2005) 2001
34. For ring-closing metathesis using vinyl acrylates, see:. Julie T., and Joelle P. Synlett 17 (2006) 2807
35. Fustero S., Sanchez-Rosello M., Rodrigo V., Pozo C.D., Sanz-Cervera J.F., and Simon A. Org. Lett. 18 (2006) 4129
36. Krafft M.E., Song E.-H., and Davoile R.J. Tetrahedron Lett. 46 (2005) 6359
37. Thorstensson F., Kvarnstrom I., Musil D., Nilsson I., and Samuelsson B. J. Med. Chem. 46 (2003) 1165
38. For similar observations see:. Liu S.-L., Shi X.-X., Xu Y.-L., Xu W., and Dong J. Tetrahedron: Asymmetry 20 (2009) 78
39. Bell R.A., and Osakwe E.N.C. Chem. Commun. (1968) 1093
40. Adrio J., Carretero J.C., Ruano J.L.G., and Cabrejas L.M.J. Tetrahedron: Asymmetry 8 (1997) 1623
41. 2O (1:1, 1 mL) and a catalytic amount of DMAP at room temperature for 6 h. Removal of solvent under reduced pressure gave a residue which was purified by column chromatography (hexane/EtOAc 9:1) to obtain the mixture of diastereomers as light yellow oil. (15/16; 68:32 ratio) (253 mg, 91%).(1S,2R,6S)-4-(Ethoxycarbonyl)-6-(4-nitrobenzoyloxy)-cyclohex-3-ene- 1,2-diyl diacetate (15):
42. Spectral data for these compounds were similar to the ones reported for them in the literature. See Ref. [24] and Supplementary data for details.