Efficient syntheses-of (-)-shikimate and (-)-quinate 3-phosphate via trans vicinal diol protection with 2,2,3,3-tetramethoxybutane (TMB) of shikimic and quinic acids

Tetrahedron Letters

Volumn 41, Issue 16, 2000, Pages 2957-2959

  Shih, Tzenge Lien ^a   Wu, Shih Hsiung ^a,b  

^a INSTITUTE OF BIOLOGICAL CHEMISTRY   (Taiwan)

^b NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

2,2,3,3 tetramethoxybutane; Quinate 3 phosphate; Quinic acid; Shikimate 3 phosphate; Shikimic acid

Indexed keywords

QUINIC ACID; SHIKIMIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROLYSIS; REACTION ANALYSIS; SYNTHESIS;

EID: 0034656282     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00280-X     Document Type: Article

References (14)

1. (a) Chahoua, L.; Baltas, M.; Gorrichon, L.; Tisnès, P.; Zedde, C. J. Org. Chem. 1992, 57, 5798.
2. (b) For racemic synthesis of 3-phosphoshikimate acid, see: Bartlett, P. A.; McQuaid, L. A. J. Am. Chem. Soc. 1984, 106, 7854.
3. (a) Montchamp, J.-L.; Tian, F.; Hart, M. E.; Frost, J. W. J. Org. Chem. 1996, 61, 3897.
4. (b) Douglas, N. L.; Ley, S. V.; Osborn, H. M. I.; Owen, D. R.; Priepke, H. W. M.; Warriner, S. L. Synlett 1996, 793.
5. (a) Shinada, T.; Yoshida, Y.; Ohfune, Y. Tetrahedron Lett. 1998, 39, 6027.
6. (b) Alves, C.; Teresa Barros, M.; Maycock, C. D.; Rita Ventura, M. Tetrahedron 1999, 55, 8443.
7. For natural product synthesis by using D-(-)-quinic acid, see review: Barco, A.; Benetti, S.; Risi, C. D.; Marchetti, P.; Pollini, G.; Zanirato, V. Tetrahedron: Asymmetry 1997, 8, 3515.
8. Shikimic acid, used for the preparation of 3, was purchased from Sigma.
9. 13C NMR data are consistent with the reported values in Ref. 3b.
10. Yu, K.-L.; Fraser-Reid, B. Tetrahedron Lett. 1988, 29, 979.
11. +-OMe, 100%).
12. +-OMe, 100%).
13. 3, 100 MHz) δ 170.4, 166.3, 133.3, 132.2, 99.7, 99.1, 68.8, 66.1, 62.9, 52.2, 48.0, 47.9, 30.0, 20.9, 17.8, 17.6.
14. Ulibarri, G.; Nadler, W.; Skrydstrup, T.; Audrain, H.; Chiaroni, A.; Riche, C.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753.