Concise syntheses of meridianins by carbonylative alkynylation and a four-component pyrimidine synthesis

Angewandte Chemie - International Edition

Volumn 44, Issue 42, 2005, Pages 6951-6956

  Karpov, Alexei S ^a   Merkul, Eugen ^a   Rominger, Frank ^a   Müller, Thomas J J ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

C C coupling; Carbonylation; Heterocycles; Multicomponent reactions; Natural products

Indexed keywords

CARBON MONOXIDE; SYNTHESIS (CHEMICAL);

C-C COUPLING; CARBONYLATIVE ALKYNYLATION; MULTICOMPONENT REACTIONS;

ORGANIC COMPOUNDS;

ALKYNE; INDOLE ALKALOID; IODINATED HYDROCARBON; PYRIMIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ISOLATION AND PURIFICATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALKYNES; CRYSTALLOGRAPHY, X-RAY; HYDROCARBONS, IODINATED; INDOLE ALKALOIDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRIMIDINES;

EID: 27544431953     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200501703     Document Type: Article

References (35)

1. For reviews, see, for example, a) "The Pyrimidines": D. J. Brown in The Chemistry of Heterocyclic Compounds, Vol. 16 (Ed.: A. Weissberger), Wiley-Interscience, New York, 1970;
2. b) "Fused Pyrimidines, Part II, The Purines": J. H. Lister in The Chemistry of Heterocyclic Compounds, Vol. 24 (Eds.: A. Weissberger, E. C. Taylor), Wiley-Interscience, New York, 1971;
3. c) M. G. Hoffmann in Houben-Weyl, Methoden der Organischen Chemie, Vol. E9 (Ed.: E. Schaumann), Thieme, Stuttgart, 1996;
4. d) D. T. Hurst in An Introduction to the Chemistry and Biochemistry of Pyrimidines, Purines and Pteridines, Wiley, Chichester, 1980;
5. e) J. T. Bojarski, J. L. Mokrosz, H. J. Bartón, M. H. Paluchowska, Adv. Heterocycl. Chem. 1985, 38, 229;
6. f) D. J. Brown in Comprehensive Heterocyclic Chemistry, Vol. 3 (Eds. : A. R. Katritzky, C. W. Rees), Pergamon, Oxford, 1984, chap. 2.13.
7. For the significance of 2,4-disubstituted pyrimidines as tyrosine kinase inhibitors see, for example, a) P. Traxler, G. Bold, E. Buchdunger, G. Caravatti, P. Furet, P. Manley, T. O'Reilly, J. Wood, J. Zimmermann, Med. Res. Rev. 2001, 21, 499;
8. b) J. Zimmermann, E. Buchdunger, H. Mett, T. Meyer, N. B. Lydon, Bioorg. Med. Chem. Lett. 1997, 7, 187.
9. L. H. Franco, E. Joffé, L. Puricelli, M. Tatian, A. M. Seldes, J. A. Palermo, J. Nat. Prod. 1998, 61, 1130.
10. M. L. Gompel, M. Leost, E. B. D. K. Joffe, L. Puricelli, L. H. Franco, J. Palermo, L. Meijer, Bioorg. Med. Chem. Lett. 2004, 14, 1703.
11. a) N. B. Perry, L. Ettouati, M. Litaudon, J. W. Blunt, M. H. G. Munro, S. Parkin, H. Hope, Tetrahedron 1994, 50, 3987;
12. b) G. Trimurtulu, D. J. Faulkner, N. B. Perry, L. Ettouati, M. Litaudon, J. W. Blunt, M. H. G. Munro, G. B. Jameson, Tetrahedron 1994, 50, 3993.
13. D. Fernández, A. Ahaidar, G. Danelón, P. Cironi, M. Marfil, O. Pérez, C. Cuevas, F. Albericio, J. A. Joule, M. Álvarez, Monatsh. Chem. 2004, 135, 615.
14. a) M. Álvarez, D. Fernández, J. A. Joule, Tetrahedron Lett. 2001, 42, 315;
15. b) A. Ahaidar, D. Fernández, G. Danelón, C. Cuevas, I. Manzanares, F. Albericio, J. A. Joule, M. Álvarez, J. Org. Chem. 2003, 68, 10 020.
16. B. Jiang, C. Yang, Heterocycles 2000, 53, 1489.
17. a) P. M. Fresneda, P. Molina, S. Delgado, J. A. Bleda, Tetrahedron Lett. 2000, 41, 4777;
18. b) P. Molina, P. M. Fresneda, S. Delgado, J. A. Bleda, Tetrahedron Lett. 2002, 43, 1005;
19. c) P. Molina, P. M. Fresneda, S. Delgado, J. Org. Chem. 2003, 68, 489.
20. P. M. Fresneda, P. Molina, J. A. Bleda, Tetrahedron 2001, 57, 2355.
21. a) A. S. Karpov, T. J. J. Müller, Org. Lett. 2003, 5, 3451;
22. b) A. S. Karpov, T. J. J. Müller, Synthesis 2003, 2815.
23. D. M. Ketcha, G. W. Gribble, J. Org. Chem. 1985, 50, 5451.
24. a) T. Kobayashi, M. Tanaka, J. Chem. Soc. Chem. Commun. 1981, 333;
25. b) K. Okuro, M. Furuune, M. Enna, M. Miura, M. Nomura, J. Org. Chem. 1993, 58, 4716;
26. c) L. Delude, A. M. Masdeu, H. Alper, Synthesis 1994, 1149;
27. d) B. C. Bishop, K. M. J. Brands, A. D. Gibb, D. J. Kennedy, Synthesis 2004, 43.
28. A. Arcadi, S. Cacchi, F. Marinelli, P. Pace, G. Sanzi, Synlett 1995, 823.
29. M. S. M. Ahmed, A. Mori, Org. Lett. 2003, 5, 3057.
30. B. Witulski, N. Buschmann, U. Bergsträsser, Tetrahedron 2000, 56, 8473.
31. 3-Iodoindoles were obtained in almost quantitative yields as beige solids still containing traces of DMF and can be stored without decomposition at 0°C under nitrogen. However, it is advisable to convert them directly to the more stable N-Boc-protected 3-iodoindoles 4, which were isolated as colorless solids by column chromatography on neutral aluminium oxide (column chromatography on silica gel leads to red color and accelerates the decomposition).
32. 2 with a full-matrix least-squares algorithm using the SHELXTL-PLUS (5.10) software package (software package SHELXTL V5.10 for structure solution and refinement,
33. -3.
34. CCDC-278205 (5d) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
35. The kinase inhibition assays were carried out in collaboration with Merck KGaA as described in S. P. Davies, H. Reddy, M. Caivano, P. Cohen, Biochem. J. 2000, 351, 95.