An improved procedure for the preparation of the β-hydroxy-α- alkyl fatty acid fragment of mycolic acids

Tetrahedron

Volumn 62, Issue 14, 2006, Pages 3221-3227

  Toschi, Gianna ^a,b   Baird, Mark S ^a  

^a BANGOR UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF PRETORIA   (South Africa)

Author keywords

Mycolic acid synthesis

Indexed keywords

BETA HYDROXY ALPHA FATTY ACID; FATTY ACID DERIVATIVE; MYCOLIC ACID; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; ENANTIOMER; METHODOLOGY; PRIORITY JOURNAL; SYNTHESIS;

EID: 33644891313     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.01.070     Document Type: Article

References (37)

1. D.E. Minnikin J. Standford The Biology of the Mycobacteria 1982 Academic San Diego 95 184
2. C.E. Barry III, R.E. Lee, K. Mdluli, A.E. Sampson, B.G. Schoeder, R.A. Slayden, and Y. Yuan Prog. Lipid Res. 37 1998 143 179
3. R.J. Heath, S.W. White, and C.O. Rock Appl. Microbiol. Biotechnol. 58 2002 695 703
4. M. Watanabe, Y. Aoyagi, H. Mitome, T. Fujita, H. Naoki, M. Ridell, and D.E. Minnikin Microbiology 148 2002 1881 1902
5. M. Watanabe, Y. Aoyagi, M. Ridell, and D.E. Minnikin Microbiology 147 2001 1825 1837
6. D.E. Minnikin, and N. Polgar Chem. Commun. 18 1966 648 649
7. C. Asselineau, G. Tocanne, and J.F. Tocanne Bull. Soc. Chim. Fr. 4 1970 1455 1459
8. C. Lacave, M.-A. Lanéelle, H. Montrozier, M.-P. Rols, and C. Asselineau Eur. J. Biochem. 163 1987 369 378
9. M. Daffé, M.A. Lanéelle, and L.V. Guillen Eur. J. Biochem. 177 1988 339 340
10. M. Daffe, M.A. Laneelle, and C. Lacave Res. Microbiol. 142 1991 397 403
11. H. Durand, M. Welby, G. Lanéelle, and J.-F. Tocanne Eur. J. Biochem. 93 1979 103 112
12. H. Durand, M. Gillois, J.-F. Tocanne, and G. Lanéelle Eur. J. Biochem. 94 1979 109 118
13. D.B. Moody, M.R. Guy, E. Grant, T.-Y. Cheng, M.B. Brenner, G.S. Besra, and S.A. Porcelli J. Exp. Med. 192 2000 965 976
14. R. Watanabe, Y.C. Yoo, K. Hata, M. Mitobe, Y. Koike, M. Nishizawa, D.M. Garcia, Y. Nobuchi, I. Hiroshi, H. Yamada, and I. Azuma Vaccine 17 1999 1484 1492
15. Y. Kitano, Y. Kobayashi, and F. Sato J. Chem. Soc., Chem. Commun. 1985 498 499
16. Y. Kobayashi, Y. Kitano, Y. Takeda, and F. Sato Tetrahedron 42 1986 2937 2943
17. M. Nishizawa, R. Minagawa, D.M. Garcia, S. Hatakeyama, and H. Yamada Tetrahedron Lett. 35 1994 5891 5894
18. M. Utaka, H. Higashi, and A. Takeda J. Chem. Soc., Chem. Commun. 1987 1368 1369
19. M. Utaka, H. Watabu, H. Higashi, T. Sakai, S. Tsuboi, and S. Torii J. Org. Chem. 55 1990 3917 3921
20. V. Ratovelomanana-Vidal, C. Girard, R. Touati, J.P. Tranchier, B.B. Hassine, and J.P. Genet Adv. Synth. Catal. 345 2003 261 274
21. J.R. Al Dulayymi, M.S. Baird, and E. Roberts J. Chem. Soc., Chem. Commun. 2003 228 229
22. Tetrahedron 61 2005 11939 11951
23. T.T. Upadhya, M.D. Nikalje, and A. Sudalai Tetrahedron Lett. 42 2001 4891 4893
24. H.C. Kolb, M.S. Vannieuwenhze, and K.B. Sharpless Chem. Rev. 94 1994 2483 2547
25. H.-S. Byun, L. He, and R. Bittman Tetrahedron 56 2000 7051 7091
26. G. Fräter, U. Müller, and W. Günther Tetrahedron 40 1984 1269 1277
27. G. Fräter Tetrahedron Lett. 22 1981 425 428
28. In the case of the homologue of (10 ) with 10 instead of nine methylene groups in the chain good yields were only achieved if the reaction was carried out as follows: Butyllithium (13.33 ml, 28 mmol, 2.1 M) was added to a stirred solution of diisopropylamine (3.73 ml, 26.66 mmol) in dry THF (120 ml) at -78°C under argon. The mixture was allowed to reach room temperature and stirred for 15 min. It was then cooled to -78°C and the ester (4.17 g, 12.12 mmol) in dry THF (45 ml) was added. The mixture was allowed to warm to -5°C over 2 h, stirred at 0-2°C for 0.5 h, then cooled to -70°C and 1-iodoprop-2-ene (1.55 ml, 17.0 mmol) and HMPA (6.32 ml, 36.4 mmol) in dry THF (10 ml) were added. The reaction was allowed to reach 0°C over 1.5 h and then quenched with aq ammonium chloride (10 ml) followed by brine (100 ml). The product was extracted with petrol-ethyl acetate (1/1, 3×100 ml). The combined organic layers were washed with water, dried and evaporated to give a pale yellow oil. Column chromatography eluting with 5:2 petrol and ethyl acetate gave the product as a colourless oil (2.56 g, 56%) (Al-Dulayymi, J. R. and Koza, G. Unpublished results).
29. Y. Wensheng, M. Yan, K. Ying, H. Zhengmao, and J. Zhendong Org. Lett. 6 2004 3217 3219
30. P.R. Blakemore J. Chem. Soc., Perkin Trans. 1 2002 2563 2585
31. A.K. Datta, K. Takayama, M.A. Nashed, and L. Anderson Carbohydr. Res. 218 1991 95 109
32. M. Villeneuvea, M. Kawaia, H. Kanashimaa, M. Watanabe, D.E. Minnikin, and H. Nakaharaa Biochim. Biophys. Acta 1715 2005 71 80
33. H. Imagawa, T. Tsuchihashi, R.K. Singh, H. Yamamoto, T. Sugihara, and M. Nishizawa Org. Lett. 5 2003 153 156
34. F. Matsuura, Y. Hamada, and T. Shioiri Tetrahedron 50 1994 11304 11314
35. B. Jakob, G. Voss, and H. Gerlach Tetrahedron: Asymmetry 7 1996 3255 3262
36. T. Arslan, and S.A. Benner J. Org. Chem. 58 1993 2260 2264
37. K. Mori, and M. Ishikura Liebigs Ann. Chem. 1989 1263 1266