The first synthesis of single enantiomers of ketomycolic acids

Tetrahedron Letters

Volumn 48, Issue 12, 2007, Pages 2165-2169

  Koza, Gani ^a   Baird, Mark S ^a  

^a BANGOR UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA METHYLCYCLOPROPANE; CYCLOPROPANE; MYCOLIC ACID; OXOMYCOLIC ACID; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER;

EID: 33847077227     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.01.100     Document Type: Article

References (44)

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31. 20
32. Prepared by methods described earlier:. Toschi G., and Baird M.S. Tetrahedron 62 (2006) 3221-3227
33. 3].
34. 3): 215.1, 173.6, 170.3, 74.1(-), 51.5(-), 49.6(-), 46.3(-), 41.1(+), 38.1(-), 37.4(+), 34.5(+), 33.0(+), 31.9(+), 31.7(+), 30.1(+), 29.72(+), 29.70(+, v br), 29.67(+), 29.65(+), 29.60(+), 29.57(+), 29.55(+), 29.51(+), 29.48(+), 29.46(+), 29.44(+), 29.39(+), 29.35(+), 28.1(+), 27.5(+), 27.4(+), 27.3 (+), 26.1(-), 25.0(+), 23.72(+), 22.68(+), 21.0(-), 19.7(-), 18.6(-), 16.4(-), 14.1(-), 10.5(+).
35. 6
36. We thank Proffessor D.E. Minnikin (Univ. of Birmingham) for providing a sample of natural ketomycolic acid.
37. Thanks are due to Mr. B. Grail, School of Biological Sciences, Bangor for running these spectra.
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40. Minnikin D.E., Dobson G., Goodfellow M., Draper P., and Magnusson M. J. Gen. Microbiol. 131 (1985) 2013
41. Prepared by a method similar to that described below for 24.
42. 22b
43. 3): 215.1, 173.6, 170.3, 74.1(-), 51.5(-), 49.6(-), 46.3(-), 41.1(+), 33.1(+), 31.9(+), 31.7(+), 30.2(+), 29.8(+), 29.70(+, v br), 29.65(+), 29.63(+), 29.60(+), 29.56(+), 29.51(+), 29.49(+), 29.46(+), 29.44(+), 29.40(+), 29.36(+), 28.7(+), 28.1(+), 27.5(+), 27.3(+), 25.0(+), 23.7(+), 22.7(+), 21.0(-), 16.4(-), 15.8(-), 14.1(-), 10.9(+).
44. 3), again consistent with partial or complete racemisation at the α-methylketone.