Concise syntheses of meridianins and meriolins using a catalytic domino amino-palladation reaction

Organic Letters

Volumn 16, Issue 3, 2014, Pages 708-711

  Walker, Scott R ^a   Czyz, Milena L ^b   Morris, Jonathan C ^b  

^a UNIVERSITY OF ADELAIDE   (Australia)

^b UNIVERSITY OF NEW SOUTH WALES   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

FUSED HETEROCYCLIC RINGS; INDOLE ALKALOID; MERIDIANIN A; MERIOLIN 3; PALLADIUM; PYRIMIDINE DERIVATIVE; SINGLE HETEROCYCLIC RINGS;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BICYCLO COMPOUNDS, HETEROCYCLIC; CATALYSIS; HETEROCYCLIC COMPOUNDS, 1-RING; INDOLE ALKALOIDS; MOLECULAR STRUCTURE; PALLADIUM; PYRIMIDINES; STEREOISOMERISM;

EID: 84893845619     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol403390m     Document Type: Article

References (47)

1. Hernandez Franco, L.; Bal de Joffe, E.; Puricelli, L.; Tatian, M.; Seldes, A. M.; Palermo, J. A. J. Nat. Prod. 1998, 61, 1130
2. Seldes, A. M.; Brasco, M. F. R.; Hernandez Franco, L.; Palermo, J. A. Nat. Prod. Res. 2007, 21, 555
3. Gompel, M.; Leost, M.; Bal de Joffe, E.; Puricelli, L.; Franco, L. H.; Palermo, J.; Meijer, L. Bioorg. Med. Chem. Lett. 2004, 14, 1703
4. Walker, S. R.; Carter, E. J.; Huff, B. C.; Morris, J. C. Chem. Rev. 2009, 109, 3080
5. Pauletti, P. M.; Cintra, L. S.; Braguine, C. G.; Da Silva Filho, A. A.; Silva, M. L. A.; Cunha, W. R.; Januário, A. H. Marine Drugs 2010, 8, 1526
6. Rossignol, E.; Debiton, E.; Fabbro, D.; Moreau, P.; Prudhomme, M.; Anizon, F. Anti-Cancer Drugs 2010, 19, 789
7. Bharate, S. B.; Yadav, R. R.; Battula, S.; Vishwakarma, R. A. Mini-Reviews Med. Chem. 2012, 12, 618
8. Bharate, S. B.; Yadav, R. R.; Vishwakarma, R. A. Med. Chem. 2013, 9, 152
9. Li, K.; McGee, L. R.; Fisher, B.; Sudom, A.; Liu, J.; Rubenstein, S. M.; Anwer, M. K.; Cushing, T. D.; Shin, Y.; Ayres, M.; Lee, F.; Eksterowicz, J.; Faulder, P.; Waszkowycz, B.; Plotnikova, O.; Farrelly, E.; Xiao, S.-H.; Chen, G.; Wang, Z. Bioorg. Med. Chem. Lett. 2013, 23, 1238
10. Giraud, F.; Alves, G.; Debiton, E.; Nauton, L.; Théry, V.; Durieu, E.; Ferandin, Y.; Meijer, L.; Anizon, F.; Pereira, E.; Moreau, P. J. Med. Chem. 2011, 54, 4474
11. Lebar, M. D.; Hahn, K. N.; Mutka, T.; Maignan, P.; McClintock, J. B.; Amsler, C. D.; Van Olphen, A.; Kyle, D. E.; Baker, B. J. Bioorg. Med. Chem. 2011, 19, 5756
12. Bharate, S. B.; Yadav, R. R.; Khan, S. I.; Tekwani, B. L.; Jacob, M. R.; Khan, I. A.; Vishwakarma, R. A. MedChemComm 2013, 4, 1042
13. Bettayeb, K.; Tirado, O. M.; Marionneau-Lambot, S.; Ferandin, Y.; Lozach, O.; Morris, J. C.; Mateo-Lozano, S.; Drückes, P.; Schächtele, C.; Kubbutat, M.; Liger, F.; Marquet, B.; Joseph, B.; Echalier, A.; Endicott, J.; Notario, V.; Meijer, L. Cancer Res. 2007, 67, 8325
14. Echalier, A.; Bettayeb, K.; Ferandin, Y.; Lozach, O.; Clement, M.; Valette, A.; Liger, F.; Marquet, B.; Morris, J. C.; Endicott, J.; Joseph, B.; Meijer, L. J. Med. Chem. 2008, 51, 735
15. Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873
16. Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875
17. Cacchi, S.; Fabrizi, G. Chem. Rev. 2011, 111, PR2215
18. Taber, D. F.; Tirunahari, P. K. Tetrahedron 2011, 67, 7195
19. Cacchi, S.; Fabrizi, G.; Goggiamani, A. Org. React. 2012, 281
20. Inman, M.; Moody, C. J. Chem. Sci. 2013, 4, 29
21. Fresneda, P. M.; Molina, P.; Delgado, S.; Bleda, J. A. Tetrahedron Lett. 2000, 41, 4777
22. Jiang, B.; Yang, C.-G. Heterocycles 2000, 53, 1489
23. Fresneda, P. M.; Molina, P.; Bleda, J. A. Tetrahedron 2001, 57, 2355
24. Franco, L. H.; Palermo, J. A. Chem. Pharm. Bull. 2003, 51, 975
25. Časar, Z.; Bevk, D.; Svete, J.; Stanovnik, B. Tetrahedron 2005, 61, 7508
26. Karpov, A. S.; Merkul, E.; Rominger, F.; Müller, T. J. J. Angew. Chem., Int. Ed. 2005, 44, 6951
27. Radwan, M. A. A.; El-Sherbiny, M. Bioorg. Med. Chem. 2007, 15, 1206
28. Rossignol, E.; Youssef, A.; Moreau, P.; Prudhomme, M.; Anizon, F. Tetrahedron 2007, 63, 10169
29. Corbel, B.; Michaud, F.; Meijer, L.; Simon, G.; Couthon-Gourves, H.; Haelters, J.-P.; Kervarec, N. J. Heterocycl. Chem. 2007, 44, 793
30. Oliveira-Campos, A. M. F.; Salaheldin, A. M.; Paz, F. A. A.; Rodrigues, L. M. ARKIVOC 2011, 11, 121
31. Merkul, E.; Schäfer, E.; Müller, T. J. J. Org. Biomol. Chem. 2011, 9, 3139
32. Sperry, J. Tetrahedron Lett. 2011, 52, 4537
33. Parsons, T. B.; Ghellamallah, C.; Male, L.; Spencer, N.; Grainger, R. S. Org. Biomol. Chem. 2011, 9, 5021
34. A notable exception is the synthesis reported by Penoni and coworkers. Tibiletti, F.; Simonetti, M.; Nicholas, K. M.; Palmisano, G.; Parravicini, M.; Imbesi, F.; Tollari, S.; Penoni, A. Tetrahedron 2010, 66, 1280
35. Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671
36. Cacchi, S.; Fabrizi, G.; Goggiamani, A. Adv. Synth. Catal. 2006, 348, 1301
37. Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L.; Pace, P. Synlett 1997, 1363
38. Arcadi, A.; Cacchi, S.; Carnicelli, V.; Marinelli, F. Tetrahedron 1994, 50, 437
39. Hassan, H. H. A. M.; Spies, H. S.; Bredenkamp, M. W. Polish J. Chem. 2000, 74, 1589
40. Cironi, P.; Tulla-Puche, J.; Barany, G.; Albericio, F.; Alvarez, M. Org. Lett. 2004, 6, 1405
41. Anderson, R. J.; Hill, J. B.; Morris, J. C. J. Org. Chem. 2005, 70, 6204
42. Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 4, 529
43. Adlington, R. M.; Baldwin, J. E.; Catterick, D.; Pritchard, G. J. J. Chem. Soc., Perkin Trans. 1 1999, 855
44. Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652
45. Callaghan, P. D.; Gibson, M. S. J. Chem. Soc. (C) 1970, 2106
46. Prepared from iodide 20 (prepared using the method of Cook and coworkers): Ma, C.; Liu, X.; Li, X.; Flippen-Anderson, J.; Yu, S.; Cook, J. M. J. Org. Chem. 2001, 66, 4525
47. Amine 18 was prepared in two steps and 65% overall yield, as described in Scheme 5, starting from commercially available amine 19. See also: Nair, R. N.; Lee, P. J.; Rheingold, A. L.; Grotjahn, D. B. Chem.-Eur. J. 2010, 16, 7992