Enantioselective synthesis of R-(+)-α and S-(-)-α-lipoic acid

Tetrahedron Letters

Volumn 45, Issue 31, 2004, Pages 6027-6028

  Chavan, Subhash P ^a   Praveen, Cherukupally ^a   Ramakrishna, G ^a   Kalkote, U R ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

cis 2 Butene 1,4 diol; Claisen orthoester rearrangement; Lipoic acid; Sharpless asymmetric dihydroxylation

Indexed keywords

ESTER; THIOCTIC ACID;

ARTICLE; DIHYDROXYLATION; ENANTIOSELECTIVITY; HYDROLYSIS; REACTION ANALYSIS; SYNTHESIS;

EID: 3142774226     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.06.027     Document Type: Article

References (21)

1. Reed L.J., Gunsalus I.C., De Busk B.G., Hornberger C.S. Jr. Science. 114:1951;93-94
2. Schmidt U., Grafen P., Altland K., Goedde H.W. Adv. Enzymol. 32:1969;423-469
3. Sigel H. Angew. Chem., Int. Ed. Engl. 21:1982;389-400
4. Reed L.J., Gunsalus I.C., Schnakenberg G.H.F., Soper Q.F., Boaz H.E., Kern S.F., Parke T.V. J. Am. Chem. Soc. 75:1953;1267-1270
5. Reed L.J., DeBusk B.G., Hornberger C.S., Gunsalus I.C. J. Am. Chem. Soc. 75:1953;1271-1273
6. Brookes M.H., Golding B.T., Howes D.A., Hudson A.T. J. Chem. Soc., Chem. Commun. 1983;1051-1053. The same group has completed a synthesis of the natural enantiomer
7. Bast A., Haenen G.R.M.M. Biochim. Biophys. Acta. 963:1988;558-561
8. Baur A., Harrer T., Penkert, Jahn G., Kalden J.R., Fleckenstein B.Klin Wocheschr. 69:1991;722-724. Chem. Abstr. 1992, 116, 207360
9. Bingfham, P. M.; Zarchar Z. PCT Int. Appl. WO 0024, 734, 2000; Chem. Abstr. 2000, 132, 3081921
10. Streeper R.S., Henriksen E.J., Tritschler H.J. Am. J. Physiol. 273(1 pt 1):1997;E185-191
11. Brookes M.H., Golding B.T., Hudson A.T. J. Chem. Soc., Perkin Trans. 1. 1988;9-12
12. Rao A.V.R., Gurjar M.K., Garyali K., Ravindranathan T. Carbohydr. Res. 148:1986;51-55
13. Rao A.V.R., Mysorekar S.V., Gurjar M.K., Yadav J.S. Tetrahedron Lett. 28:1987;2183-2186
14. Page P.C.B., Rayner C.M., Sutherland I.O. J. Chem. Soc., Chem. Commun. 1986;1408-1409
15. Menon R.B., Kumar M.A., Ravindranathan T. Tetrahedron Lett. 28:1987;5313-5314
16. Laxmi Y.R.S., Iyengar D.S. Synthesis. 1996;594-596
17. Adger B., Bes M.T., Grogan G., McCaque R., Pedragosa M.S., Roberts S.M., Villa R., Wan P.W.H., Willetts A.J. Bioorg. Med. Chem. 5:1997;253-261
18. Upadhya T.T., Nikalje M.D., Sudalai A. Tetrahedron Lett. 42:2001;4891-4893. and references cited therein
19. Elliott J.D., Steele J., Johnson W.S. Tetrahedron Lett. 26:1985;2535-2538
20. Chavan S.P., Praveen C. Tetrahedron Lett. 45:2004;421-423
21. 3) δ:14.08, 27.98, 33.86, 37.75, 59.84, 72.49, 72.89, 73.22, 121.45, 127.48, 127.74, 128.25, 137.00, 148.14, 166.11 ppm.