Efficient synthesis of (S,S)-ethambutol from L-methionine

Tetrahedron

Volumn 58, Issue 49, 2002, Pages 9765-9767

  Stauffer, Christina S ^a   Datta, Apurba ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

Desulfurization; Dimerization; Ethambutol; L methionine; Tuberculostatic

Indexed keywords

DIAMIDE; ETHAMBUTOL; METHIONINE; NICKEL; OXALYL DIAMIDE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; DESULFURIZATION; DIMERIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL;

EID: 0037010761     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01308-X     Document Type: Article

References (16)

1. (a) Wilkinson, R. G.; Shepherd, R. G.; Thomas, J. P.; Baughn C. J. Am. Chem. Soc. 1961, 83, 2212-2213.
2. (b) Shepherd, R. G.; Wilkinson, R. G. J. Med. Chem. 1962, 5, 823-835.
3. (c) Wilkinson R.G., Cantrall M., Shepherd R.G. J. Med. Chem. 5:1962;835-845.
4. Pablos-Méndez A., Ravigilone M.C., Laszlo A., Binkin N., Reider H.L., Bustreo F., Cohn D.L., Lambregts-van Weezenbeek C.S., Kim S.J., Chavlet P., Nunn P. N. Engl. J. Med. 338:1998;1641-1649.
5. Takayama K., Armstrong E.L., Kunugi K.A., Kilburn J.O. Antimicrob. Agents Chemother. 16:1979;240-242.
6. (a) For a review, see: Blessington B. Impact of Stereochemistry on Drug Development and Use. Chem. Anal. (New York). 142:1997;235-261.
7. (b) For a recent study on ethambutol SAR, see: Hausler H., Kawakami R.P., Mlaker E., Severn W.B., Stütz A.E. Bioorg. Med. Chem. Lett. 11:2001;1679-1681.
8. (a) Bernardi L., Foglio M., Giardino P., Temperilli A. Chim. Ind. (Milan). 36:1974;347.
9. (b) Butala I., Karlovic G. Liebigs Ann. Chem. 1976;1455-1464.
10. (c) Han J.O., Choe I. Chosun Minjujui Iumin Konghwaguk Kwahagwon Tongbo. 27:1979;88.
11. Chem. Abstr. 1979, 91, 140265u.
12. (d) Bevianakatti H.S., Newadkar R.V. Tetrahedron: Asymmetry. 1:1990;583-586.
13. Trost B.M., Bunt R.C., Lemoine R.C., Calkins T.L. J. Am. Chem. Soc. 122:2000;5968-5976.
14. (a) Datta A., Ravi Kumar J.S., Roy S. Tetrahedron. 57:2001;1169-1173.
15. (b) Datta A., Veeresa G. J. Org. Chem. 65:2000;7609-7611. and references therein.
16. Pavlic A.A., Adkins H. J. Am. Chem. Soc. 68:1946;1471.