The synthesis of single enantiomers of mycobacterial ketomycolic acids containing cis-cyclopropanes

Tetrahedron

Volumn 65, Issue 49, 2009, Pages 10214-10229

  Koza, Gani ^a   Theunissen, Cornelia ^a   Al Dulayymi, Juma'a R ^a   Baird, Mark S ^a  

^a BANGOR UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

18 (TERT BUTYLDIMETHYLSILANYLOXY) 19 METHYLHEPTATRIACONTAN 1 OL; 18 (TERT BUTYLDIMETHYLSILANYLOXY) 19 METHYLHEPTATRIACONTANAL; 2 (3 BENZYLOXY 1 HYDROXYPROPYL)PENT 4 ENOIC ACID METHYL ESTER; 2 [1 (TERT BUTYLDIMETHYLSILANYLOXY) 15 (5 PHENYL 5H TETRAZOL YLSULFANYL)PENTADECYL]HEXACOSANOIC ACID METHYL ESTER; 2 [1 (TERT BUTYLDIMETHYLSILANYLOXY) 3 HYDROXYPROPYL]HEXACOSANOIC ACID METHYL ESTER; 2 [1 (TERT BUTYLDIMETHYLSILANYLOXY) 3 OXOPROPYL]HEXACOSANOIC ACID METHYL ESTER; 2 [1 ACETOXY 15 (5 PHENYL 5H TETRAZOL YLSULFANYL)PENTADECYL]HEXACOSANOIC ACID METHYL ESTER; 2 [1 ACETOXY 16 [2 [19 (TERTBUTYLDIMETHYLSILANYLOXY) 20 METHYLOCTATRIA CONTYL]CYCLOPROPYL]OCTADECYL]HEXACOSANOIC ACID METHYL ESTER; 2 [1 ACETOXY 16 [2 [19 (TERTBUTYLDIMETHYLSILANYLOXY) 20 METHYLOCTATRIACONTYL]CYCLOPROPYL]OCTADECYL]HEXACOSANOIC ACID METHYL ESTER; 2 [1 HYDROXY 15 (5 PHENYL 5H TETRAZOL YLSULFANYL)PENTADECYL]HEXACOSANOIC ACID METHYL ESTER; 2 [1 HYDROXY 16 [2 (19 HYDROXY 20 METHYLOCTATRIACONTYL)CYCLOPROPYL]HEXADECYL]HEXACOSANOIC ACID; 2 [15 BROMO 1 (TERT BUTYLDIMETHYLSILANYLOXY)PENTADECYL]HEXACOSANOIC ACID METHYL ESTER; 2 [19 (TERT BUTYLDIMETHYLSILANYLOXY) 2' METHYLOCTATRIACONTYL]CYCLOPROPANE CARBALDEHYDE; 2 [19 (TERT BUTYLDIMETHYLSILANYLOXY) 2' METHYLOCTATRIACONTYL]CYCLOPROPYL]METHANOL; 2 [3 BENZYLOXY 1 (TERT BUTYLDIMETHYLSILANYLOXY)PROPYL]HEXACOSANOIC ACID METHYL ESTER; 2 [3 BENZYLOXY 1 (TERT BUTYLDIMETHYLSILANYLOXY)PROPYL]PENT 4 ENOIC ACID METHYL ESTER; 2,2 DIMETHYLPROPIONIC ACID 10 (1 PHENYL 1H TETRAZOL 5 SULFONYL)DECYLESTER; 2,2 DIMETHYLPROPIONIC ACID 10[ 2 [ 19 (TERT BUTYLDIMETHYLSILANYLOXY) 20 METHYLOCTATRIACONTYL]CYCLOPRCYCLOPROPYL]DECYLESTER; 2,2 DIMETHYLPROPIONIC ACID 18 (TERT BUTYLDIMETHYLSILANYLOXY) 19 METHYLHEPTATRIACONTYLESTER; 3 ACETOXY 5 BENZYLOXYPENTANOIC ACID; 5 BENZYLOXY 3 (TERT BUTYLDIMETHYLSILANYLOXY) 2 (2 OXOETHYL)PENTANOIC ACID METHYL ESTER; 5 BENZYLOXY 3 HYDROXYPENTANOIC ACID METHYL ESTER; 8 (TERT BUTYLDIMETHYLSILANYLOXY) 9 METHYLHEPTACOSAN 1 OL; 8 (TERT BUTYLDIMETHYLSILANYLOXY) 9 METHYLHEPTACOSANAL; ACETIC ACID 1 (2 BENZYLOXYETHYL) BUT 3 ENYLESTER; ANTIINFECTIVE AGENT; BUTYRIC ACID 2 [19 (TERT BUTYLDIMETHYLSILANYLOXY) 2' METHYLOCTATRIACONTYL]CYCLOPROPYLMETHYL ESTER; CYCLOPROPANE DERIVATIVE; MYCOLIC ACID; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; PRIORITY JOURNAL; STEREOISOMERISM;

EID: 70350517433     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.09.099     Document Type: Article

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45. We thank Prof. D.E.Minnikin (Univ. of Birmingham) for providing samples of natural ketomycolic acid fractions.
46. Thanks are due to Mr B.Grail, School of Biological Sciences, Bangor for running these spectra.