Step-Economical Synthesis of the Marine Ascidian Antibiotics Cadiolide A, B, and D

Journal of Organic Chemistry

Volumn 80, Issue 1, 2015, Pages 681-684

  Boukouvalas, John ^a   Thibault, Charles ^a  

^a UNIVERSITÉ LAVAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANIC COMPOUNDS;

BUILDING BLOCKES; DIELS-ALDER CYCLOADDITIONS; EFFICIENT SYNTHESIS; KNOEVENAGEL CONDENSATION; NATURAL PRODUCTS; ONE POT; OXAZOLES; PROTECTING GROUP;

CYCLOADDITION;

ANTIBIOTIC AGENT; BUTENOLIDE; CADIOLIDE A; CADIOLIDE B; CADIOLIDE D; OXAZOLE; UNCLASSIFIED DRUG; ANTIINFECTIVE AGENT; GAMMA BUTYROLACTONE;

ARTICLE; ASCIDIACEA; BROMINATION; CLICK CHEMISTRY; CYCLOADDITION; DEMETHYLATION; DIELS ALDER REACTION; HYDROLYSIS; KNOEVENAGEL CONDENSATION; NONHUMAN; ONE POT SYNTHESIS; SYNTHESIS; ANALOGS AND DERIVATIVES; ANIMAL; AQUATIC SPECIES; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; UROCHORDATA;

4-BUTYROLACTONE; ANIMALS; ANTI-BACTERIAL AGENTS; AQUATIC ORGANISMS; CYCLIZATION; MOLECULAR STRUCTURE; UROCHORDATA;

EID: 84931263163     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo502503w     Document Type: Article

References (49)

1. World Health Organization. First Comprehensive Global Report on Antimicrobial Resistance, 2014, http://www.who.int/drugresistance/documents/surveillancereport/en/.
2. Hede, K. Nature 2014, 509, S2-S3
3. Jarvis, L. M. Chem. Eng. News 2014, 92 (24) 9-14
4. Kobayashi, S. D.; DeLeo, F. R. Nature Med. 2011, 17, 168-169
5. Podoll, J. D.; Liu, Y.; Chang, L.; Walls, S.; Wang, W.; Wang, X. Proc. Natl. Acad. Sci. U.S.A. 2013, 110, 15573-15578
6. Kirst, H. A. Expert Opin. Drug Discov. 2013, 8, 479-493
7. Cui, L.; Tominaga, E.; Neoh, H.; Hiramatsu, K. Antimicrob. Agents Chemother. 2006, 50, 1079-1082
8. Gardete, S.; Tomasz, A. J. Clin. Invest. 2014, 124, 2836-2840
9. Smith, C. J.; Hettich, R. L.; Jompa, J.; Tahir, A.; Buchanan, M. V.; Ireland, C. M. J. Org. Chem. 1998, 63, 4147-4150
10. Wang, W.; Kim, H.; Nam, S.-J.; Rho, B. J.; Kang, H. J. Nat. Prod. 2012, 75, 2049-2054
11. Won, T. H.; Jeon, J.-e.; Kim, S.-H.; Lee, S.-H.; Rho, B. J.; Oh, D.-C.; Oh, K.-B.; Shin, J. J. Nat. Prod. 2012, 75, 2055-2061
12. Ahn, C.-H.; Won, T. H.; Kim, H.; Shin, J.; Oh, K.-B. Bioorg. Med. Chem. Lett. 2013, 23, 4099-4101
13. Smitha, D.; Kumar, M. M. K.; Ramana, H.; Rao, D. V. Nat. Prod. Res. 2014, 28, 12-17
14. Miao, S.; Andersen, R. J. J. Org. Chem. 1991, 56, 6275-6280
15. Ortega, M. J.; Zubía, E.; Ocaña, J. M.; Naranjo, S.; Salvá, J. Tetrahedron 2000, 56, 3963-3967
16. Sun, H.; Huang, H.; Zhang, D.; Feng, E.; Qian, W.; Zhang, L.; Chen, K.; Liu, H. Adv. Synth. Catal. 2011, 353, 1413-1419
17. Park, K. H.; Kim, S. Y.; Chung, Y. K. Org. Biomol. Chem. 2005, 3, 395-398
18. Kotora, M.; Negishi, E. Synthesis 1997, 121-128
19. Boukouvalas, J.; Lachance, N.; Ouellet, M.; Trudeau, M. Tetrahedron Lett. 1998, 39, 7665-7668
20. Bellina, F.; Anselmi, C.; Viel, S.; Mannina, L.; Rossi, R. Tetrahedron 2001, 57, 9997-10007
21. Bellina, F.; Anselmi, C.; Rossi, R. Tetrahedron Lett. 2002, 43, 2023-2027
22. Kar, A.; Argade, N. P. Synthesis 2005, 2284-2286
23. Chavan, S. P.; Pathak, A. B.; Pandey, A.; Kalkote, U. R. Synth. Commun. 2007, 37, 4253-4263
24. Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Sferrazza, A. Synlett 2009, 1277-1280
25. Boukouvalas, J.; McCann, L. C. Tetrahedron Lett. 2010, 51, 4636-4639
26. Tale, N. P.; Shelke, A. V.; Tiwari, G. B.; Thorat, P. B.; Karade, N. N. Helv. Chim. Acta 2012, 95, 852-857
27. Barbosa, L. C. A.; Maltha, C. R. A.; Lage, M. R.; Barcelos, R. C.; Donaì, A.; Varneiro, J. W. M.; Forlani, G. J. Agric. Food Chem. 2012, 60, 10555-10563
28. Pereira, U. A.; Barbosa, L. C. A.; Maltha, C. R. A.; Demuner, A. J.; Masood, M. A.; Pimenta, A. L. Eur. J. Med. Chem. 2014, 82, 127-138
29. Bellina, F.; Anselmi, C.; Martina, F.; Rossi, R. Eur. J. Org. Chem. 2003, 2290-2302
30. Zhang, R.; Iskander, G.; da Silva, P.; Chan, D.; Vignevich, V.; Nguyen, V.; Bhadbhade, M. M.; Black, D. S.; Kumar, N. Tetrahedron 2011, 67, 3010-3016
31. Boukouvalas, J.; Pouliot, M. Synlett 2005, 343-345
32. Peixoto, P. A.; Boulangé, A.; Leleu, S.; Franck, X. Eur. J. Org. Chem. 2013, 3316-3327
33. Liang, J.; Hu, W.; Tao, P.; Jia, Y. J. Org. Chem. 2013, 78, 5810-5815
34. Roy, S.; Davydova, M. P.; Pal, R.; Gilmore, K.; Tolstikov, G. A.; Vasilevsky, S. F.; Alabugin, I. V. J. Org. Chem. 2011, 76, 7482-7490
35. Waldo, J. P.; Larock, R. C. J. Org. Chem. 2007, 72, 9643-9647
36. Kim, W.; Park, K.; Park, A.; Choe, J.; Lee, S. Org. Lett. 2013, 15, 1654-1657
37. Alternatively, oxazole 14 can be inexpensively prepared on a large scale from d,l -alanine: Dean, A.; Ferlin, M. G.; Brun, P.; Castagliuolo, I.; Badocco, D.; Pastore, P.; Venzo, A.; Bombi, G. G.; Di Marco, V. B. Dalton Trans. 2008, 1689-1697
38. Boukouvalas, J.; Loach, R. P. Org. Lett. 2013, 15, 4912-4914
39. Boukouvalas, J.; Thibault, C.; Loach, R. P. Synlett 2014, 25, 2139-2142
40. Grigg, R.; Jackson, J. L. J. Chem. Soc. C 1970, 552-556
41. Levin, J. I.; Laakso, L. M. Oxazole Diels-Alder Reactions. In Oxazoles: Synthesis, Reactions, and Spectroscopy; Palmer, D. C., Ed.; Wiley-VCH: Weinheim, 2003; Part A, Vol. 60, Chapter 3, pp 417-472.
42. For the use of such a process on a multikilogram scale, see: Hutton, J.; Potts, B.; Southern, P. F. Synth. Commun. 1979, 9, 789-797
43. Kumar, L.; Sharma, V.; Mahajan, T.; Agarwal, D. D. Org. Process Res. Dev. 2010, 14, 174-179
44. Boukouvalas, J.; Beltrán, P. P.; Lachance, N.; Coîté, S.; Maltais, F.; Pouliot, M. Synlett 2007, 219-222
45. Reddy, L. R.; Corey, E. J. Tetrahedron Lett. 2005, 46, 927-929
46. Bordwell, F. G.; Fried, H. E. J. Org. Chem. 1991, 56, 4218-4223
47. Li, W.; Fedosov, S. N.; Tan, T.; Xu, X.; Guo, Z. ACS Catal. 2014, 4, 3294-3300
48. Burgoyne, A. R.; Meijboom, R. Catal. Lett. 2013, 143, 563-571
49. Kulchat, S.; Meguellati, K.; Lehn, J.-M. Helv. Chim. Acta 2014, 97, 1219-1236