A short asymmetric total synthesis of chloramphenicol using a selectively protected 1,2-diol

Tetrahedron Letters

Volumn 46, Issue 10, 2005, Pages 1743-1746

  Boruwa, Joshodeep ^a   Borah, Jagat C ^a   Gogoi, Siddhartha ^a   Barua, Nabin C ^a  

^a REGIONAL RESEARCH LABORATORY   (India)

Author keywords

1,2 Diol; Chloramphenicol; Nitrite ester; Selective protection

Indexed keywords

ALCOHOL DERIVATIVE; ANTIBIOTIC AGENT; CHLORAMPHENICOL; FLUORAMPHENICOL; THIAMPHENICOL; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 13744259805     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.01.039     Document Type: Article

References (23)

1. K. Nakanishi, T. Goto, S. Ito, S. Natoro, and S. Nozoe Natural Products Chemistry Vol. 3 1983 Oxford University Press Oxford
2. P. Garner, and S. Ramakanth J. Org. Chem. 51 1986 2609 2612
3. I. Ojima Enantioselective Synthesis of β-Amino Acids 1996 VCD New York
4. J. Erlich, Q.R. Bartz, R.M. Smith, P.R. Josley, and P.R. Burkholder Science 106 1947 417 418
5. G. Bhaskar, V.S. Kumar, and B.V. Rao Tetrahedron: Asymmetry 15 2004 1279 1283 and references cited therein
6. B. Kalita, M.S. Bezbarua, N.C. Barua, and G. Bez Synlett 2001 1411 1414
7. S. Gogoi, N.C. Barua, and B. Kalita Tetrahedron Lett. 45 2004 5577 5579
8. J. Boruwa, J.C. Borah, B. Kalita, and N.C. Barua Tetrahedron Lett. 39 2004 7355 7358
9. K. Jarowicki, and P.J. Kocienski J. Chem. Soc., Perkin Trans. 1 18 2001 2109 2121 and references cited therein
10. B.-Z. Zheng, M. Yamaguchi, H. Dei, S.-I. Kusaka, K. Matsui, and O. Yonemitsu Tetrahedron Lett. 41 2000 6441 6445
11. O.I. Sutherland Comprehensive Organic Chemistry Vol. 2, Part 7 1979 Pergamon 356
12. P. Sarmah, and N.C. Barua Tetrahedron Lett. 30 1989 4703 4704
13. P. Sarmah, and N.C. Barua Tetrahedron Lett. 31 1990 4065 4066
14. B.K. Sarma, and N.C. Barua Tetrahedron 47 1991 8587 8600
15. J.-N. Denis, A. Correa, and A.E. Green J. Org. Chem. 55 1990 1957 1959
16. P.R. Fleming, and K.B. Sharpless J. Org. Chem. 56 1991 2869 2875
17. R.V. Hoffman, and H. Kim J. Org. Chem. 56 1991 6759 6764
18. The enantiomeric excess was measured by HPLC analysis carried out on a Waters 510 HPLC system. Chiracel OD packed in a 4.6 mm i.d × 250 mm SS column was used. Isocratic elution was applied with a mobile phase n-hexane 90% and isopropanol 10% at a flow rate of 0.8 mL/min and pressure of 125 psi with UV monitoring at 243 nm
19. 4: C, 48.00; H, 4.03; N, 22.39. Found: C 48.17; H, 4.09; N, 22.28
20. 4), the solvent evaporated and the crude residue purified by silica gel column chromatography
21. N. Irako, Y. Hamada, and T. Shioiri Tetrahedron 48 1992 7251 7264
22. J. Controulis, M.C. Rebstock, and H.M. Crooks J. Am. Chem. Soc. 71 1949 2463 2468
23. A.A. Al-Bader, and H.A. El-Obeid Chloramphenicol K. Florey Analytical Profiles of Drug Substances Vol. 15 1986 Academic Orlando 701