Total synthesis of caerulomycin C via the halogen dance reaction

Organic Letters

Volumn 4, Issue 14, 2002, Pages 2385-2388

  Sammakia, Tarek ^a   Stangeland, Eric L ^a   Whitcomb, Mark C ^a  

^a UNIVERSITY OF COLORADO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,2' BIPYRIDINE; CERULOMYCIN; DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; HALOGEN;

ARTICLE; CATALYSIS; CHEMISTRY; STREPTOMYCES; SYNTHESIS;

2,2'-DIPYRIDYL; CATALYSIS; HALOGENS; INDICATORS AND REAGENTS; STREPTOMYCES;

EID: 0037062903     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026135m     Document Type: Article

References (33)

1. Sammakia, T.; Hurley, T. B. J. Am. Chem. Soc. 1996, 118, 8967. Sammakia, T.; Hurley, T. B. J. Org. Chem. 1999, 64, 4652. Sammakia, T.; Hurley, T. B. J. Org. Chem. 2000, 65, 974.
2. Sammakia, T.; Hurley, T. B. J. Am. Chem. Soc. 1996, 118, 8967. Sammakia, T.; Hurley, T. B. J. Org. Chem. 1999, 64, 4652. Sammakia, T.; Hurley, T. B. J. Org. Chem. 2000, 65, 974.
3. Sammakia, T.; Hurley, T. B. J. Am. Chem. Soc. 1996, 118, 8967. Sammakia, T.; Hurley, T. B. J. Org. Chem. 1999, 64, 4652. Sammakia, T.; Hurley, T. B. J. Org. Chem. 2000, 65, 974.
4. For reviews of the halogen dance reaction, see: Bunnett, J. F. Acc. Chem. Res. 1972, 5, 139. Frohlich, J. Bull. Soc. Chim. Belg. 1996, 105, 615. Froehlich, J. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Oxford: New York, 1994; Vol. 6, pp 1-35. For leading references to more recent work, see: Comins, D. L.; Saha, J. Tetrahedron Lett. 1995, 36, 7995. Trécourt, F.; Mallet, M.; Mongin, O.; Quéguiner, G. J. Org. Chem. 1994, 59, 6173. Guillier, F.; Nivoliers, F.; Godard, A.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1994, 35, 6489. Rocca, P.; Cochennec, C.; Marsais, F.; Thomas-dit-Dumont, L.; Mallet, M.; Godard, A.; Quéguiner, G. J. Org. Chem. 1993, 58, 7832. Marsais, F.; Pineau, P.; Nivolliers, F.; Mallet, M.; Turck, A.; Godard, A.; Quéguiner, G. J. Org. Chem. 1992, 57, 565.
5. For reviews of the halogen dance reaction, see: Bunnett, J. F. Acc. Chem. Res. 1972, 5, 139. Frohlich, J. Bull. Soc. Chim. Belg. 1996, 105, 615. Froehlich, J. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Oxford: New York, 1994; Vol. 6, pp 1-35. For leading references to more recent work, see: Comins, D. L.; Saha, J. Tetrahedron Lett. 1995, 36, 7995. Trécourt, F.; Mallet, M.; Mongin, O.; Quéguiner, G. J. Org. Chem. 1994, 59, 6173. Guillier, F.; Nivoliers, F.; Godard, A.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1994, 35, 6489. Rocca, P.; Cochennec, C.; Marsais, F.; Thomas-dit-Dumont, L.; Mallet, M.; Godard, A.; Quéguiner, G. J. Org. Chem. 1993, 58, 7832. Marsais, F.; Pineau, P.; Nivolliers, F.; Mallet, M.; Turck, A.; Godard, A.; Quéguiner, G. J. Org. Chem. 1992, 57, 565.
6. For reviews of the halogen dance reaction, see: Bunnett, J. F. Acc. Chem. Res. 1972, 5, 139. Frohlich, J. Bull. Soc. Chim. Belg. 1996, 105, 615. Froehlich, J. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Oxford: New York, 1994; Vol. 6, pp 1-35. For leading references to more recent work, see: Comins, D. L.; Saha, J. Tetrahedron Lett. 1995, 36, 7995. Trécourt, F.; Mallet, M.; Mongin, O.; Quéguiner, G. J. Org. Chem. 1994, 59, 6173. Guillier, F.; Nivoliers, F.; Godard, A.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1994, 35, 6489. Rocca, P.; Cochennec, C.; Marsais, F.; Thomas-dit-Dumont, L.; Mallet, M.; Godard, A.; Quéguiner, G. J. Org. Chem. 1993, 58, 7832. Marsais, F.; Pineau, P.; Nivolliers, F.; Mallet, M.; Turck, A.; Godard, A.; Quéguiner, G. J. Org. Chem. 1992, 57, 565.
7. For reviews of the halogen dance reaction, see: Bunnett, J. F. Acc. Chem. Res. 1972, 5, 139. Frohlich, J. Bull. Soc. Chim. Belg. 1996, 105, 615. Froehlich, J. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Oxford: New York, 1994; Vol. 6, pp 1-35. For leading references to more recent work, see: Comins, D. L.; Saha, J. Tetrahedron Lett. 1995, 36, 7995. Trécourt, F.; Mallet, M.; Mongin, O.; Quéguiner, G. J. Org. Chem. 1994, 59, 6173. Guillier, F.; Nivoliers, F.; Godard, A.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1994, 35, 6489. Rocca, P.; Cochennec, C.; Marsais, F.; Thomas-dit-Dumont, L.; Mallet, M.; Godard, A.; Quéguiner, G. J. Org. Chem. 1993, 58, 7832. Marsais, F.; Pineau, P.; Nivolliers, F.; Mallet, M.; Turck, A.; Godard, A.; Quéguiner, G. J. Org. Chem. 1992, 57, 565.
8. For reviews of the halogen dance reaction, see: Bunnett, J. F. Acc. Chem. Res. 1972, 5, 139. Frohlich, J. Bull. Soc. Chim. Belg. 1996, 105, 615. Froehlich, J. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Oxford: New York, 1994; Vol. 6, pp 1-35. For leading references to more recent work, see: Comins, D. L.; Saha, J. Tetrahedron Lett. 1995, 36, 7995. Trécourt, F.; Mallet, M.; Mongin, O.; Quéguiner, G. J. Org. Chem. 1994, 59, 6173. Guillier, F.; Nivoliers, F.; Godard, A.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1994, 35, 6489. Rocca, P.; Cochennec, C.; Marsais, F.; Thomas-dit-Dumont, L.; Mallet, M.; Godard, A.; Quéguiner, G. J. Org. Chem. 1993, 58, 7832. Marsais, F.; Pineau, P.; Nivolliers, F.; Mallet, M.; Turck, A.; Godard, A.; Quéguiner, G. J. Org. Chem. 1992, 57, 565.
9. For reviews of the halogen dance reaction, see: Bunnett, J. F. Acc. Chem. Res. 1972, 5, 139. Frohlich, J. Bull. Soc. Chim. Belg. 1996, 105, 615. Froehlich, J. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Oxford: New York, 1994; Vol. 6, pp 1-35. For leading references to more recent work, see: Comins, D. L.; Saha, J. Tetrahedron Lett. 1995, 36, 7995. Trécourt, F.; Mallet, M.; Mongin, O.; Quéguiner, G. J. Org. Chem. 1994, 59, 6173. Guillier, F.; Nivoliers, F.; Godard, A.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1994, 35, 6489. Rocca, P.; Cochennec, C.; Marsais, F.; Thomas-dit-Dumont, L.; Mallet, M.; Godard, A.; Quéguiner, G. J. Org. Chem. 1993, 58, 7832. Marsais, F.; Pineau, P.; Nivolliers, F.; Mallet, M.; Turck, A.; Godard, A.; Quéguiner, G. J. Org. Chem. 1992, 57, 565.
10. For reviews of the halogen dance reaction, see: Bunnett, J. F. Acc. Chem. Res. 1972, 5, 139. Frohlich, J. Bull. Soc. Chim. Belg. 1996, 105, 615. Froehlich, J. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Oxford: New York, 1994; Vol. 6, pp 1-35. For leading references to more recent work, see: Comins, D. L.; Saha, J. Tetrahedron Lett. 1995, 36, 7995. Trécourt, F.; Mallet, M.; Mongin, O.; Quéguiner, G. J. Org. Chem. 1994, 59, 6173. Guillier, F.; Nivoliers, F.; Godard, A.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1994, 35, 6489. Rocca, P.; Cochennec, C.; Marsais, F.; Thomas-dit-Dumont, L.; Mallet, M.; Godard, A.; Quéguiner, G. J. Org. Chem. 1993, 58, 7832. Marsais, F.; Pineau, P.; Nivolliers, F.; Mallet, M.; Turck, A.; Godard, A.; Quéguiner, G. J. Org. Chem. 1992, 57, 565.
11. For reviews of the halogen dance reaction, see: Bunnett, J. F. Acc. Chem. Res. 1972, 5, 139. Frohlich, J. Bull. Soc. Chim. Belg. 1996, 105, 615. Froehlich, J. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Oxford: New York, 1994; Vol. 6, pp 1-35. For leading references to more recent work, see: Comins, D. L.; Saha, J. Tetrahedron Lett. 1995, 36, 7995. Trécourt, F.; Mallet, M.; Mongin, O.; Quéguiner, G. J. Org. Chem. 1994, 59, 6173. Guillier, F.; Nivoliers, F.; Godard, A.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1994, 35, 6489. Rocca, P.; Cochennec, C.; Marsais, F.; Thomas-dit-Dumont, L.; Mallet, M.; Godard, A.; Quéguiner, G. J. Org. Chem. 1993, 58, 7832. Marsais, F.; Pineau, P.; Nivolliers, F.; Mallet, M.; Turck, A.; Godard, A.; Quéguiner, G. J. Org. Chem. 1992, 57, 565.
12. For a review of metalations of azaaromatics, see: Queguiner, G.; Marsais, F.; Sniekus, V.; Epsztajn, J. In Advances in Heterocydic Chemistry; Katritzky, A. R., Ed.; Acdemic Press: San Diego, 1991; Vol. 52, pp 187-304.
13. The intermediacy of an aryne can be ruled out since the expected products (addition of the amine base to the aryne) are not observed.
14. For examples, see: Arzel, E.; Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron Lett. 1998, 39, 6465. Bury, P.; Hareau, G.; Kociensky, P.; Dhanak, D. Tetrahedron 1994, 29, 8793. Sauter, F.; Froehlich, H.; Kalt, W. Synthesis 1989, 771.
15. For examples, see: Arzel, E.; Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron Lett. 1998, 39, 6465. Bury, P.; Hareau, G.; Kociensky, P.; Dhanak, D. Tetrahedron 1994, 29, 8793. Sauter, F.; Froehlich, H.; Kalt, W. Synthesis 1989, 771.
16. For examples, see: Arzel, E.; Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron Lett. 1998, 39, 6465. Bury, P.; Hareau, G.; Kociensky, P.; Dhanak, D. Tetrahedron 1994, 29, 8793. Sauter, F.; Froehlich, H.; Kalt, W. Synthesis 1989, 771.
17. (a) Isolation: Funk, A.; Divekar, P. Can. J. Microbiol. 1959, 5, 317.
18. (b) Structure determination and biological activity: McInnes, A. G.; Smith, D. G.; Wright, J. L. C.; Vining, L. C. Can. J. Chem. 1977, 55, 4159.
19. (c) Synthesis: Trécourt, F.; Gervais, B.; Mallet, M.; Quéguiner, G. J. Org. Chem. 1996, 61, 1673.
20. Snieckus, V. Chem. Rev. 1990, 90, 879.
21. Gschwend, H. w.; Rodriguez, H. R. Heteroatom Facilitated Lithiations. Org. React. (N.Y.) 1979, 26, 1-30. Mongin, F.; Queguiner, G. Tetrahedron 2001, 57, 4059.
22. Gschwend, H. w.; Rodriguez, H. R. Heteroatom Facilitated Lithiations. Org. React. (N.Y.) 1979, 26, 1-30. Mongin, F.; Queguiner, G. Tetrahedron 2001, 57, 4059.
23. Sundberg, R. J.; Jiang, S. Org. Prep. Proced. Int. 1997, 29, 117.
24. A methoxy group can be a better kinetic ortho-directing group than a chlorine atom; however, chlorine can be a better thermodynamic carbanion stabilizing group. For a discussion, see: Iwao, M. J. Org. Chem. 1990, 55, 3622. For a related competition experiment, see: Slocum, D. W.; Dietzel, P. Tetrahedron Lett. 1999, 40, 1823. Iwao ascribed the kinetic preference for deprotonation ortho-to a methoxy group to complexation to the alkyllithium base; however, Collum has recently provided evidence that complexation-induced proximity effects are not important in the lithiation of anisole. See; Chadwick, S. T.; Rennels, R. A.; Rutherford, J. L.; Collum, D. B. J. Am. Chem. Soc. 2000, 122, 8640.
25. A methoxy group can be a better kinetic ortho-directing group than a chlorine atom; however, chlorine can be a better thermodynamic carbanion stabilizing group. For a discussion, see: Iwao, M. J. Org. Chem. 1990, 55, 3622. For a related competition experiment, see: Slocum, D. W.; Dietzel, P. Tetrahedron Lett. 1999, 40, 1823. Iwao ascribed the kinetic preference for deprotonation ortho-to a methoxy group to complexation to the alkyllithium base; however, Collum has recently provided evidence that complexation-induced proximity effects are not important in the lithiation of anisole. See; Chadwick, S. T.; Rennels, R. A.; Rutherford, J. L.; Collum, D. B. J. Am. Chem. Soc. 2000, 122, 8640.
26. A methoxy group can be a better kinetic ortho-directing group than a chlorine atom; however, chlorine can be a better thermodynamic carbanion stabilizing group. For a discussion, see: Iwao, M. J. Org. Chem. 1990, 55, 3622. For a related competition experiment, see: Slocum, D. W.; Dietzel, P. Tetrahedron Lett. 1999, 40, 1823. Iwao ascribed the kinetic preference for deprotonation ortho-to a methoxy group to complexation to the alkyllithium base; however, Collum has recently provided evidence that complexation-induced proximity effects are not important in the lithiation of anisole. See; Chadwick, S. T.; Rennels, R. A.; Rutherford, J. L.; Collum, D. B. J. Am. Chem. Soc. 2000, 122, 8640.
27. Nucleophilic aromatic substitution at the 3-or 5-position of pyridines is known to be more difficult than at the 2-or 4-position. See: Schofield, K. Hetero-Aromatic Nitrogen Compounds Pyrroles and Pyridines; Plenum: New York, 1967; p 244.
28. Keegstra, M. A.; Peters, T. H. A.; Brandsma, L. Tetrahedron 1992, 48, 3633.
29. This product is contaminated with about 5% of the reduced compound 27, which is difficult to separate at this stage, but is readily removed in the next step.
30. 3, CuI, DMF, 80 °C). See: Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585. Liebeskind, L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359.
31. 3, CuI, DMF, 80 °C). See: Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585. Liebeskind, L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359.
32. 3, CuI, DMF, 80 °C). See: Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585. Liebeskind, L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359.
33. Note Added in Proof: While this manuscript was undergoing review, a new synthesis of caerulomycin C appeared. See: Mongin, F.; Trecourt, F.; Gervais, B.; Mongin, O.; Queguiner, G. J. Org. Chem. 2002, 67, 3272.