An Alternative Approach to Aminodiols from Baylis-Hillman Adducts. Stereoselective Synthesis of Chloramphenicol, Fluoramphenicol and Thiamphenicol
Keywords:
Chloramphenicol, Baylis-Hillman, fluoramphenicol, thiamphenicol, α-hydroxymethylketonesAbstract
Abstract. We describe herein a new approach for the stereoselective synthesis of broad spectrum antibiotics from Baylis-Hillman adducts. The strategy is based on the preparation of an ene-carbamate directly from a Baylis-Hillman adduct using a Curtius rearrangement reaction. Stereoselective hydroboration furnished a mixture of diastereoisomeric aminoalcohols (syn and anti). After chromatographic separation, the syn diastereoisomer was directly transformed into the antibiotics.
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1. Aguilar, L.; Gimenez, M. J.; Garcia-Rey, C.; Martin, J. E.; J. Antimicrob. Chemother. 2002, 50, 93.
2. Lautenbach, E.; Gould, C. V.; La Rosa, L. A.; Marr, A. M.; Fishman, N. O.; Becker, W. B.; Nachamkin, I.; Int. J. Antimicrob. Agents 2004, 23, 200; Boulos, A.; Rolain, J. M.; Raoult, D.; Antimicrob. Agents. Chemother. 2004, 48, 747; Zhanel, G. G.; Laing, N. M.; Nichol, K. A.; Palatvek, L. P.; Noreddin, A.; Hisanaga, T.; Johnson, J. L.; Hoban, D. J.; J. Antimicrob. Chemother. 2003, 52, 382; Cunrie, B. J.; Eur. Respi. J. 2003, 22, 542.
3. Xaplanteri, M. A.; Andreou, A.; Dinos, G. P.; Kalpaxis, D. L.; Nucleic Acids Res. 2003, 32, 5074; Isenberg, S. J.; J. AAPOS 2003, 7, 307.
4. Ungheri, D.; Licciardello, L.; PCT Int. Appl. WO 060344, 2001 (CA 135:162487); Colombo, G.; Ungheri, D.; Licciardello, L.; Giromondo, M.; Drago, L. PCT Int. Appl. WO 076585, 2001 (CA 135: 198756).
5. Ehrlich, J.; Bartz, Q. R.; Smith, R. M.; Joslyn, D. A.; Burkholder, P. R.; Science 1947, 106, 417; Bartz, Q.R.; J. Biol. Chem. 1948, 172, 445; Smith, R. M.; Joslyn, D. A.; Gruhzit, O. M.; McLean, W. I.; Penner, M. A.; Ehrlich, J.; J. Bacteriol. 1948, 55, 425; Bartz, Q.R.; J. Clin. Invest. 1949, 28, 1051.
6. For examples of classical industrial synthesis of chloramphenicol and related antibiotics, see: Ehrlich, J.; Kirk- Othmer Encyclopedia of Chemical Technology, John Wiley & Sons: New York, 1978, vol. 2., p. 920.
7. For some syntheses of racemic chloramphenicol, see: Controulis, J.; Rebstock, M. C.; Crooks, Jr., H. M.; J. Am. Chem. Soc. 1949, 71, 2463; Long, L. M.; Troutman, H. D.; J. Am. Chem. Soc. 1949, 71, 2469 and 2473; Ehrhart, G.; Siedel, W.; Nahm, H.; Chem. Ber. 1957, 90, 2088; Horak, V.; Moezik, F.; Klein, R. F. X.; Giordano, C.; Synthesis 1984, 839; Hazra, B. G.; Pore, V. S.; Maybhate, S. P.; Synth. Commun. 1997, 27, 1857.
8. For some chiral syntheses of chloramphenicol and fluoramphenicol, see: Chenevert, R.; Thiboutot, S.; Synthesis 1989, 444; Schollkopf, U.;Beulshausen, T.; Liebigs Ann. Chem. 1989, 223; Rao, A. V. R.; Rao, S. P.; Bhanu, M. N.; J. Chem. Soc., Chem.Commun. 1992, 859; Lou, B.-L.; Zhang, Y.-Z.; Dai, L.-X.; Chem. Ind. 1993, 7, 249; Easton, C. J.; Hutton, C. A.; Merrett, M. C.; Tiekink, E. R. T.; Tetrahedron 1996, 52, 7025; Veeresa, G.; Datta, A.; Tetrahedron Lett. 1998, 39, 8503; Corey, E. J.; Choi, S.; Tetrahedron Lett. 2000, 41, 2765; Park, J. N.; Ko, S. Y.; Koh, H. Y.; Tetrahedron Lett. 2000, 41, 5553; Loncaric, C.; Wulff, W. D.; Org. Lett. 2001, 3, 3675; Baskhar, G.; Kumar, V.S.; Rao, B.V.; Tetrahedron:Asymmetry 2004, 15, 1279.
9. For some racemic syntheses of thiamphenicol, see: McCombie, S. W.; Nagabhushan, T. L.; Tetrahedron Lett. 1987, 28, 5395; Giordano, C.; Cavicchioli, S.;Levi, S.; Villa, M.; Tetrahedron Lett. 1988, 29, 5561.
10. For some asymmetric syntheses of thiamphenicol and florfenicol, see: Giordano, C.; Cavicchioli, S.; Levi, S.; Villa, M.; J. Org. Chem. 1991, 56, 6114; Davis, F. A.; Zhou, P.;
Tetrahedron Lett. 1994, 35, 7525; Wu, G.-Z.; Tormos, W. I.; PTC Int. Appl.WO 94/14764, 1994 (CA 121: 133722); Gennari, C.; Pain, G.; Tetrahedron Lett. 1996, 37, 3747; Wu, G.-Z.; Schumacher, D. P.; Tormos, W.; Clark, J. E.; Murphy, B. L.; J. Org. Chem. 1997, 62, 2996; Gennari, C.; Vulpetti, A.;
Pain, G.; Tetrahedron 1997, 53, 5909; Kaptein, B.;Dooren, T. J. G. M. V.; Boesten, W. H. J.; Sonke, T.; Duchateau, A. L. L.; Broxterman, Q. B.; Kamphuis, J.; Org. Process Res. Dev. 1998, 2, 10; Nagabhushan, T.L.; U. S. Patent 4 235 892, 1980 (CA 94: 139433).
11. Rossi, R.C.; Coelho, F.; Tetrahedron Lett. 2002, 43, 2797.
12. Coelho, F.; Veronese, D.; Lopes, E.C.S.; Rossi, R.C.; Tetrahedron Lett. 2003, 44, 5731.
13. For comprehensive reviews on the Baylis-Hillman reaction see: Basavaiah, D.; Rao, A. J.; Satyanarayama, T.; Chem. Rev. 2003, 103, 811; Almeida, W. P.; Coelho, F.; Quim. Nova 2000, 23, 98 (CA 132: 236562e); Ciganek, E.; Org. React. 1997, 51, 201; Basavaiah, D.; Rao, P. D.;. Hyma, R. S.; Tetrahedron 1996, 52, 8001. For some new insights about the mechanism of the Baylis-Hillman reaction see: Santos, L.S.; Pavam, C.H. Almeida, W.P.; Coelho, F.; Eberlin, M.N.; Angew. Chem. Int.
Ed. 2004, 43, 4330.
14. For some examples of the application of Baylis-Hillman adducts as starting material for the synthesis of natural products see: Almeida, W. P.; Coelho, F.; Tetrahedron Lett. 2003, 44, 937;
Feltrin, M. A.; Almeida, W. P.; Synth. Commun. 2003, 33, 1141; Mateus, C. R.; Feltrin, M. P.; Costa, A. M.; Coelho, F.; Almeida, W. P.; Tetrahedron 2001, 57, 6901; Iwabuchi, Y.; Furukawa, M.; Esumi, T.; Hatakeyama, S.; Chem. Commun. 2001, 2030; Iwabuchi, Y.; Sugihara, T.; Esumi, T.; Hatakeyama, S.; Tetrahedron Lett. 2001, 42, 7867; Masunari, A.; Trazzi, G.; Ishida, E.; Coelho, F.; Almeida, W. P.; Synth. Commun. 2001, 31, 2100; Ameer, F.; Drewes, S. E.; Houston-McMillan, M. S.; Kaye, P.T.; S. Afr. J. Chem. 1986, 39, 57; Hofmann, H. M. R.; Rabe, J.; Helv. Chim. Acta 1984, 67, 413; Hofmann, H. M. R.; Rabe, J.; J. Org. Chem. 1985, 50, 3849; Drewes, S. E.; Emslie, N. D.; J. Chem. Soc. Perkin Trans. 1 1982, 2079.
15. Bergmeier, S.C.; Tetrahedron 2000, 56, 2561 and references cited therein; Gonzalez-Resende, M.E.; Jorda-Gregori, M.E.; Sepulveda-Arques, J.; Orena, M.; Tetrahedron:Asymmetry 2004, 15, 419 and references cited therein; Beardsley, D. A.; Fisher, G. B.; Goralski, C. T.; Nicholson, L. W.; Singaram, B.; Tetrahedron Lett. 1994, 35, 1511; Moody, M. H.; Kaptein, B.; Broxterman, Q. B.; Boesten, W. H. J.; Kamphuis, J.; Tetrahedron Lett. 1994, 35, 1777; Sasai, H.; Kim, W.; Suzuki, T.; Shibasaki, M.; Tetrahedron Lett. 1994, 35, 6123.
16. Almeida, W. P.; Coelho, F. Tetrahedron Lett. 1998, 39, 8609; Coelho, F.; Almeida, W. P.; Mateus, C. R.; Veronese, D.; Lopes, E. C. S.; Silveira, G. P. C.; Rossi, R. C.; Pavam, C. H.; Tetrahedron 2002, 58, 7437.
17. Braibante, M.E.F.; Braibante, H.S.; Costenaro, J.H.; Synthesis 1999, 943; van Well, R.M.; Overkleeft, H.S.; van Boom, J.H.; Coop, J.H.; Wang, J.B.; Wang, N.Y.; van der Marel, G.A.;
Overhand, M.; Eur. J. Org. Chem. 2003, 9, 1704; Kedrowski, B.L.; J. Org. Chem. 2003, 68, 5403; Lu, Y.H.; Taylor, R.T.; Heterocycles 2004, 62, 869; O’Connor, P.D.; Mander, L.N.; McLachlan, N.W.; Org. Lett. 2004, 6, 703.
18. Jackson, R.F.W.; Standen, S.P.; Clegg, W.; McCamley, A.; Tetrahedron Lett. 1992, 33, 6197 and references cited therein; Hoffmann, R.W.; Chem. Rev. 1989, 89, 1841; Kahn, S.D.; Pau, C.F.; Chamberlin, A.R.; Hehre, W. J.; J. Am. Chem. Soc. 1987, 109, 650 and references cited therein; Coelho, F.; Almeida, W. P.; Mateus, C. R.; Furtado, L. D.; Gouveia, J. C. F.; ARKIVOC 2003, X, 443; Mateus, C.R.; Almeida, W. P.; Coelho, F.; Tetrahedron Lett. 2000, 41, 2533.
19. Cutler, R.A.; Stenger, R.J.; Suter, C.M.; J. Am. Chem. Soc. 1952, 74, 5475.
20. For some examples of carbamates prepared from Baylis-Hillman adducts, see: Ciclosi, M.; Fava, C.; Galeazzi, R.; Orena, M.; Sepulveda-Arques, J.; Tetrahedron Lett. 2002, 43, 2199;
Mamaghami, M.; Badrian, A.; Tetrahedron Lett. 2004, 45, 1547; Xu, L. W.; Xia, C. G.; Tetrahedron Lett. 2004, 45, 4507.
21. For some industrial strategies for the resolution of racemic mixtures of chloramphenicol and for the inversion of of (2S, 3S) enantiomer, see: Coppi, L.; Giordano, C.; Langoni, A.; Panossian, S. In Chirality in Chemistry II; Collins, A. N.; Sheldrake, G. N; Crosby, J., eds., Wiley: Chichester, 1997, p. 353-362; Dick, H.; Gradel, W. –D.; Weber, M.; D.E. Patent 3543021, 1987 (CA 107: 197794).
22. Iwabuchi, Y.; Nakatami, M.; Yokoyama, N.; Hatakeyama, S.; J. Am. Chem. Soc. 1999, 121, 10219.
2. Lautenbach, E.; Gould, C. V.; La Rosa, L. A.; Marr, A. M.; Fishman, N. O.; Becker, W. B.; Nachamkin, I.; Int. J. Antimicrob. Agents 2004, 23, 200; Boulos, A.; Rolain, J. M.; Raoult, D.; Antimicrob. Agents. Chemother. 2004, 48, 747; Zhanel, G. G.; Laing, N. M.; Nichol, K. A.; Palatvek, L. P.; Noreddin, A.; Hisanaga, T.; Johnson, J. L.; Hoban, D. J.; J. Antimicrob. Chemother. 2003, 52, 382; Cunrie, B. J.; Eur. Respi. J. 2003, 22, 542.
3. Xaplanteri, M. A.; Andreou, A.; Dinos, G. P.; Kalpaxis, D. L.; Nucleic Acids Res. 2003, 32, 5074; Isenberg, S. J.; J. AAPOS 2003, 7, 307.
4. Ungheri, D.; Licciardello, L.; PCT Int. Appl. WO 060344, 2001 (CA 135:162487); Colombo, G.; Ungheri, D.; Licciardello, L.; Giromondo, M.; Drago, L. PCT Int. Appl. WO 076585, 2001 (CA 135: 198756).
5. Ehrlich, J.; Bartz, Q. R.; Smith, R. M.; Joslyn, D. A.; Burkholder, P. R.; Science 1947, 106, 417; Bartz, Q.R.; J. Biol. Chem. 1948, 172, 445; Smith, R. M.; Joslyn, D. A.; Gruhzit, O. M.; McLean, W. I.; Penner, M. A.; Ehrlich, J.; J. Bacteriol. 1948, 55, 425; Bartz, Q.R.; J. Clin. Invest. 1949, 28, 1051.
6. For examples of classical industrial synthesis of chloramphenicol and related antibiotics, see: Ehrlich, J.; Kirk- Othmer Encyclopedia of Chemical Technology, John Wiley & Sons: New York, 1978, vol. 2., p. 920.
7. For some syntheses of racemic chloramphenicol, see: Controulis, J.; Rebstock, M. C.; Crooks, Jr., H. M.; J. Am. Chem. Soc. 1949, 71, 2463; Long, L. M.; Troutman, H. D.; J. Am. Chem. Soc. 1949, 71, 2469 and 2473; Ehrhart, G.; Siedel, W.; Nahm, H.; Chem. Ber. 1957, 90, 2088; Horak, V.; Moezik, F.; Klein, R. F. X.; Giordano, C.; Synthesis 1984, 839; Hazra, B. G.; Pore, V. S.; Maybhate, S. P.; Synth. Commun. 1997, 27, 1857.
8. For some chiral syntheses of chloramphenicol and fluoramphenicol, see: Chenevert, R.; Thiboutot, S.; Synthesis 1989, 444; Schollkopf, U.;Beulshausen, T.; Liebigs Ann. Chem. 1989, 223; Rao, A. V. R.; Rao, S. P.; Bhanu, M. N.; J. Chem. Soc., Chem.Commun. 1992, 859; Lou, B.-L.; Zhang, Y.-Z.; Dai, L.-X.; Chem. Ind. 1993, 7, 249; Easton, C. J.; Hutton, C. A.; Merrett, M. C.; Tiekink, E. R. T.; Tetrahedron 1996, 52, 7025; Veeresa, G.; Datta, A.; Tetrahedron Lett. 1998, 39, 8503; Corey, E. J.; Choi, S.; Tetrahedron Lett. 2000, 41, 2765; Park, J. N.; Ko, S. Y.; Koh, H. Y.; Tetrahedron Lett. 2000, 41, 5553; Loncaric, C.; Wulff, W. D.; Org. Lett. 2001, 3, 3675; Baskhar, G.; Kumar, V.S.; Rao, B.V.; Tetrahedron:Asymmetry 2004, 15, 1279.
9. For some racemic syntheses of thiamphenicol, see: McCombie, S. W.; Nagabhushan, T. L.; Tetrahedron Lett. 1987, 28, 5395; Giordano, C.; Cavicchioli, S.;Levi, S.; Villa, M.; Tetrahedron Lett. 1988, 29, 5561.
10. For some asymmetric syntheses of thiamphenicol and florfenicol, see: Giordano, C.; Cavicchioli, S.; Levi, S.; Villa, M.; J. Org. Chem. 1991, 56, 6114; Davis, F. A.; Zhou, P.;
Tetrahedron Lett. 1994, 35, 7525; Wu, G.-Z.; Tormos, W. I.; PTC Int. Appl.WO 94/14764, 1994 (CA 121: 133722); Gennari, C.; Pain, G.; Tetrahedron Lett. 1996, 37, 3747; Wu, G.-Z.; Schumacher, D. P.; Tormos, W.; Clark, J. E.; Murphy, B. L.; J. Org. Chem. 1997, 62, 2996; Gennari, C.; Vulpetti, A.;
Pain, G.; Tetrahedron 1997, 53, 5909; Kaptein, B.;Dooren, T. J. G. M. V.; Boesten, W. H. J.; Sonke, T.; Duchateau, A. L. L.; Broxterman, Q. B.; Kamphuis, J.; Org. Process Res. Dev. 1998, 2, 10; Nagabhushan, T.L.; U. S. Patent 4 235 892, 1980 (CA 94: 139433).
11. Rossi, R.C.; Coelho, F.; Tetrahedron Lett. 2002, 43, 2797.
12. Coelho, F.; Veronese, D.; Lopes, E.C.S.; Rossi, R.C.; Tetrahedron Lett. 2003, 44, 5731.
13. For comprehensive reviews on the Baylis-Hillman reaction see: Basavaiah, D.; Rao, A. J.; Satyanarayama, T.; Chem. Rev. 2003, 103, 811; Almeida, W. P.; Coelho, F.; Quim. Nova 2000, 23, 98 (CA 132: 236562e); Ciganek, E.; Org. React. 1997, 51, 201; Basavaiah, D.; Rao, P. D.;. Hyma, R. S.; Tetrahedron 1996, 52, 8001. For some new insights about the mechanism of the Baylis-Hillman reaction see: Santos, L.S.; Pavam, C.H. Almeida, W.P.; Coelho, F.; Eberlin, M.N.; Angew. Chem. Int.
Ed. 2004, 43, 4330.
14. For some examples of the application of Baylis-Hillman adducts as starting material for the synthesis of natural products see: Almeida, W. P.; Coelho, F.; Tetrahedron Lett. 2003, 44, 937;
Feltrin, M. A.; Almeida, W. P.; Synth. Commun. 2003, 33, 1141; Mateus, C. R.; Feltrin, M. P.; Costa, A. M.; Coelho, F.; Almeida, W. P.; Tetrahedron 2001, 57, 6901; Iwabuchi, Y.; Furukawa, M.; Esumi, T.; Hatakeyama, S.; Chem. Commun. 2001, 2030; Iwabuchi, Y.; Sugihara, T.; Esumi, T.; Hatakeyama, S.; Tetrahedron Lett. 2001, 42, 7867; Masunari, A.; Trazzi, G.; Ishida, E.; Coelho, F.; Almeida, W. P.; Synth. Commun. 2001, 31, 2100; Ameer, F.; Drewes, S. E.; Houston-McMillan, M. S.; Kaye, P.T.; S. Afr. J. Chem. 1986, 39, 57; Hofmann, H. M. R.; Rabe, J.; Helv. Chim. Acta 1984, 67, 413; Hofmann, H. M. R.; Rabe, J.; J. Org. Chem. 1985, 50, 3849; Drewes, S. E.; Emslie, N. D.; J. Chem. Soc. Perkin Trans. 1 1982, 2079.
15. Bergmeier, S.C.; Tetrahedron 2000, 56, 2561 and references cited therein; Gonzalez-Resende, M.E.; Jorda-Gregori, M.E.; Sepulveda-Arques, J.; Orena, M.; Tetrahedron:Asymmetry 2004, 15, 419 and references cited therein; Beardsley, D. A.; Fisher, G. B.; Goralski, C. T.; Nicholson, L. W.; Singaram, B.; Tetrahedron Lett. 1994, 35, 1511; Moody, M. H.; Kaptein, B.; Broxterman, Q. B.; Boesten, W. H. J.; Kamphuis, J.; Tetrahedron Lett. 1994, 35, 1777; Sasai, H.; Kim, W.; Suzuki, T.; Shibasaki, M.; Tetrahedron Lett. 1994, 35, 6123.
16. Almeida, W. P.; Coelho, F. Tetrahedron Lett. 1998, 39, 8609; Coelho, F.; Almeida, W. P.; Mateus, C. R.; Veronese, D.; Lopes, E. C. S.; Silveira, G. P. C.; Rossi, R. C.; Pavam, C. H.; Tetrahedron 2002, 58, 7437.
17. Braibante, M.E.F.; Braibante, H.S.; Costenaro, J.H.; Synthesis 1999, 943; van Well, R.M.; Overkleeft, H.S.; van Boom, J.H.; Coop, J.H.; Wang, J.B.; Wang, N.Y.; van der Marel, G.A.;
Overhand, M.; Eur. J. Org. Chem. 2003, 9, 1704; Kedrowski, B.L.; J. Org. Chem. 2003, 68, 5403; Lu, Y.H.; Taylor, R.T.; Heterocycles 2004, 62, 869; O’Connor, P.D.; Mander, L.N.; McLachlan, N.W.; Org. Lett. 2004, 6, 703.
18. Jackson, R.F.W.; Standen, S.P.; Clegg, W.; McCamley, A.; Tetrahedron Lett. 1992, 33, 6197 and references cited therein; Hoffmann, R.W.; Chem. Rev. 1989, 89, 1841; Kahn, S.D.; Pau, C.F.; Chamberlin, A.R.; Hehre, W. J.; J. Am. Chem. Soc. 1987, 109, 650 and references cited therein; Coelho, F.; Almeida, W. P.; Mateus, C. R.; Furtado, L. D.; Gouveia, J. C. F.; ARKIVOC 2003, X, 443; Mateus, C.R.; Almeida, W. P.; Coelho, F.; Tetrahedron Lett. 2000, 41, 2533.
19. Cutler, R.A.; Stenger, R.J.; Suter, C.M.; J. Am. Chem. Soc. 1952, 74, 5475.
20. For some examples of carbamates prepared from Baylis-Hillman adducts, see: Ciclosi, M.; Fava, C.; Galeazzi, R.; Orena, M.; Sepulveda-Arques, J.; Tetrahedron Lett. 2002, 43, 2199;
Mamaghami, M.; Badrian, A.; Tetrahedron Lett. 2004, 45, 1547; Xu, L. W.; Xia, C. G.; Tetrahedron Lett. 2004, 45, 4507.
21. For some industrial strategies for the resolution of racemic mixtures of chloramphenicol and for the inversion of of (2S, 3S) enantiomer, see: Coppi, L.; Giordano, C.; Langoni, A.; Panossian, S. In Chirality in Chemistry II; Collins, A. N.; Sheldrake, G. N; Crosby, J., eds., Wiley: Chichester, 1997, p. 353-362; Dick, H.; Gradel, W. –D.; Weber, M.; D.E. Patent 3543021, 1987 (CA 107: 197794).
22. Iwabuchi, Y.; Nakatami, M.; Yokoyama, N.; Hatakeyama, S.; J. Am. Chem. Soc. 1999, 121, 10219.
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