Syntheses of (-)-isocitric acid lactone and (-)-homoisocitric acid. A new method of conversion of alkynylsilanes into the alkynyl thioether and corresponding carboxylic acids

Journal of Organic Chemistry

Volumn 61, Issue 5, 1996, Pages 1817-1821

  Schmitz, Carole ^a   Rouanet Dreyfuss, Anne Claire ^a   Tueni, Marie ^a   Biellmann, Jean François ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; HOMOISOCITRIC ACID; ISOCITROLACTONE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; TECHNIQUE;

EID: 0029932569     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951062o     Document Type: Article

References (34)

1. Plaut, G. W. E.; Sung S. C. J. Biol. Chem. 1954, 207, 305
2. Rose, I. A.; O'Connell, E. L. J. Biol. Chem . 1967, 242, 1870.
3. Ochoa, S. Enzymes 1951, 929.
4. Plaut, G. W. E.; Sung, S. C. Methods Enzymol. 1955, 1, 710.
5. Fittig, R.; Miller, H. E. Ann. Chem. 1889, 255, 43.
6. Wislicenus, W.; Nassauer, M. Ann. Chem. 1885, 285, 1.
7. (a) Greenstein, J. P. J. Biol. Chem. 1935, 109, 529.
8. (b)Greenstein, J. P. J. biol. Chem. 1936, 116, 463.
9. Kaneko, T.; Katsura, H. Chem. Ind. (London) 1960, 1188.
10. 2O, c 0.985) for the enantiomer) Aebi, J. D.; Sutter, M. A.; Wasmuth, D.; Seebach, D. Liebigs Ann. Chem. 1983, 2114.
11. Seebach, D.; Wasmuth, D. Helv. Chem. Acta 1980, 63, 197.
12. Strassman, M.; Ceci, L. N. J. Biol. Chem. 1966, 241, 5401.
13. Strassman, M.; Ceci, L. N. J Biol. Chem. 1965, 240, 4357.
14. Yamashita, M. J. Org. Chem. 1958, 23, 835.
15. D -8 to -13 (c 1.22, acetone). Chilina, K.; Thomas, U.; Tucci, A. F.; McMichael, K. D., Stevens, C. M. Biochemistry 1969, 8, 2846.
16. Febrer, M. A.; Gomis, P.; Pascual, J. An. R. Soc. Esp. Fis. Quim. 1964, 60B, 671.
17. Rowley, B.; Tucci, A. F. Arch. Biochem. Biophys. 1970, 141, 499.
18. Schmitz, C. Ph.D. Thesis, ULP, 1992.
19. Schmitz, C.; Rouanet-Dreyfuss, A. C.; Tueni, M.; Biellmann, J. F. Tetrahedron Lett. 1992, 33, 4911.
20. Rouanet-Dreyfuss, A. C. Ph.D. Thesis, ULP, 1989.
21. Jones, T. K.; Denmark, S. E. Org. Synth. 1985, 64, 182.
22. Miller, R. B. Synth. Commun. 1972, 2, 267.
23. Zibuck, R.; Seebach, D. Helv. Chem. Acta 1988, 71, 237.
24. Zweifel, G.; Backlund, S. J. J. Am. Chem. Soc. 1977, 99, 3184.
25. McDonald, R. N.; Schwab, P. A. J. Am. Chem. Soc. 1964, 86, 4866.
26. Tamao, K.; Kumada, M. Tetrahedron Lett. 1984, 25, 321.
27. Moriarty, R. M.; Vaid, R. K.; Duncan, M. P.; Vaid, B. K. Tetrahedron Lett. 1987, 28, 2845.
28. Abrams, S. R. Can. J. Chem. 1983, 61, 2423.
29. Cooke, F.; Moerck, R.; Schwindemann, J.; Magnus, P. J. Org. Chem. 1980, 45, 1046.
30. Cunico, R. F.; Dexheimer, E. M. J. Am. Chem. Soc. 1972, 94, 2868.
31. Newman, M. S. J. Am. Chem Soc. 1953, 75, 4740.
32. Billimoria, J. D.; MacLagan, N. F. J. Chem. Soc. 1954, 3257
33. Casara, P.; Danzin, C.; Metcalf, B.; Jung, M. J. Chem. Soc., Perkin Trans. 1 1985, 2201.
34. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd, ed.; Pergamon Press: Oxford, 1988.