An efficient synthetic route to 2-(1,2-dithiolan-3-yl)acetic acid. Trisnorlipoic acid and amide derivatives

Tetrahedron Letters

Volumn 38, Issue 33, 1997, Pages 5785-5788

  Chen, Yaun Shek ^a   Lawton, Richard G ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DITHIOLANE DERIVATIVE; 2 (1,2 DITHIOLAN 3 YL)ACETIC ACID; ACETIC ACID DERIVATIVE; THIOCTIC ACID; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030837654     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01319-1     Document Type: Article

References (25)

1. Reviews: Schmidt, U.; Grafen, P.; Goedde, H. W. Angew. Chem. Int. Ed. 1965, 4, 846; Reed, L. J. "Organic Sulfur Compounds" Vol I, Pergamon Press, London, 1961, page 443.
2. Reviews: Schmidt, U.; Grafen, P.; Goedde, H. W. Angew. Chem. Int. Ed. 1965, 4, 846; Reed, L. J. "Organic Sulfur Compounds" Vol I, Pergamon Press, London, 1961, page 443.
3. Reed, L. J.; Gunsalus, I. C.; Schnakenberg, G. H. F.; Soper, Q. F.; Boaz, H. E.; Kern, S. F.; Parks, T.V. J. Am. Chem. Soc. 1953, 75, 1267.
4. Sanadi, D. R.; Langely, M.; Searls, R. L. J. Biol. Chem. 1959, 234, 178.
5. Massey, V.; Gibson, Q. H.; Veeger, C. Biochem. J. 1960, 77, 341.
6. Wilkinson, K. D.; Williams, C. H., Jr. J. Biol. Chem. 1979, 254, 852.
7. Li, T. T. T.; Weaver, M. J. J. Am. Chem. Soc. 1984, 106, 6107. Cheng, Q.; Brajter-Toth, A. Anal. Chem. 1992 64 1998-2000. Hickman, J. J.; Ofer, D.; Laibinis, P. E.; Whitsides, G. M.; Wrighton, M. S. Science 1991, 252, 688.
8. Li, T. T. T.; Weaver, M. J. J. Am. Chem. Soc. 1984, 106, 6107. Cheng, Q.; Brajter-Toth, A. Anal. Chem. 1992 64 1998-2000. Hickman, J. J.; Ofer, D.; Laibinis, P. E.; Whitsides, G. M.; Wrighton, M. S. Science 1991, 252, 688.
9. Li, T. T. T.; Weaver, M. J. J. Am. Chem. Soc. 1984, 106, 6107. Cheng, Q.; Brajter-Toth, A. Anal. Chem. 1992 64 1998-2000. Hickman, J. J.; Ofer, D.; Laibinis, P. E.; Whitsides, G. M.; Wrighton, M. S. Science 1991, 252, 688.
10. Eberle, M.; Lawton, R. G. Helv. Chim. Acta. 1988, 71, 1974.
11. Bulman Page, P. C.; Rayner, C. M.; Sutherland, I. O. Chem. commun. 1986, 1408.
12. Tsuji, J.; Yasuda, H.; Mandai, T. J. Org. Chem. 1978, 43, 3606.
13. Lewis, B. A.; Raphael, R. A. J. Chem. Soc. 1962, 4263.
14. Braude, E. A.; Linstesd, R.P.; Wooldridge, R. H. J. Chem. Soc. 1956, 3074.
15. Bullock, M. W.; Brockman, J. A., Jr.; Patterson, E. L.; Pierce, J. V.; Von Sultza, M. H.; Saunders, F.; Stokstad, E. E. R. J. Am. Chem. Soc. 1954, 76, 1828.
16. 2: C,46.67; H.5.42. Found: C,46.38; H.5.23.
17. +: 309.0466. Found: 309.0467.
18. +: 236.0177. Found: 236.0183.
19. +: 163.9966. Found: 163.9972.
20. Like lipoic acid this product upon standing, even in the refrigerator, polymerizes to a gummy material through disulfide exchange. The depolymerization to monomeric acid can be accomplished through solution in NaOH, acidification, extraction and solvent evaporation. See Thomas, R. C.; Reed, L. J. J. Am. Chem. Soc. 1956, 78, 6148.
21. Sakakibara, S.; Inukai, N. Bull. Chem. Soc. Japan 1964, 37, 1231.
22. 2: C, 46.30; H, 3.89; N, 4.91. Found: C, 46.23; H, 4.00; N, 4.77
23. 2: C,56.88;H,5.97;N,5.53. Found: C,56.76; H,5.94; N,5.37.
24. 2: C,36.78; H,5.56; N,8.58. Found: C,36.45; H,5.20; N,8.47
25. +: 220.0340. Found: 220.0347