Total synthesis of (±)-platencin

Organic Letters

Volumn 13, Issue 14, 2011, Pages 3698-3701

  Yoshimitsu, Takehiko ^a   Nojima, Shoji ^a   Hashimoto, Masashi ^a   Tanaka, Tetsuaki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOPHENOL DERIVATIVE; ANTIINFECTIVE AGENT; PLATENCIN; POLYCYCLIC HYDROCARBON;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

AMINOPHENOLS; ANTI-BACTERIAL AGENTS; CYCLIZATION; MOLECULAR STRUCTURE; POLYCYCLIC COMPOUNDS; STEREOISOMERISM;

EID: 79960180106     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2013439     Document Type: Article

References (56)

1. For selected reviews on the chemistry of platencin and platensimycin, see: Palanichamy, K.; Kaliappan, K. P. Chem. Asian J. 2010, 5, 668-703
2. Lu, X.; You, Q. Curr. Med. Chem. 2010, 17, 1139-1155
3. Harsh, P.; O'Doherty, G. A. Chemtracts 2009, 22, 31-40
4. Tiefenbacher, K.; Mulzer, J. Angew. Chem., Int. Ed. 2008, 47, 2548-2555
5. Selected papers on isolation of platencin and its congeners: Jayasuriya, H.; Herath, K. B.; Zhang, C.; Zink, D. L.; Basilio, A.; Genilloud, O.; Diez, M. T.; Vicente, F.; Gonzalez, I.; Salazar, O.; Pelaez, F.; Cummings, R.; Ha, S.; Wang, J.; Singh, S. B. Angew. Chem., Int. Ed. 2007, 46, 4684-4688
6. Wang, J.; Kodali, S.; Lee, S. H.; Galgoci, A.; Painter, R.; Dorso, K.; Racine, F.; Motyl, M.; Hernandez, L.; Tinney, E.; Colletti, S.; Herath, K.; Cummings, R.; Salazar, O.; Gonzalez, I.; Basilio, A.; Vicente, F.; Genilloud, O.; Pelaez, F.; Jayasuriya, H.; Young, K.; Cully, D.; Singh, S. B. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 7612-7616
7. Singh, S. B.; Ondeyka, J. G.; Herath, K. B.; Zhang, C.; Jayasuriya, H.; Zink, D. L.; Parthasarathy, G.; Becker, J. W.; Wang, J.; Soisson, S. M. Bioorg. Med. Chem. Lett. 2009, 19, 4756-4759
8. Zhang, C.; Ondeyka, J.; Dietrich, L.; Gailliot, F. P.; Hesse, M.; Lester, M.; Dorso, K.; Motyl, M.; Ha, S. N.; Wang, J. Bioorg. Med. Chem. 2010, 18, 2602-2610
9. Yu, Z.; Smanski, M. J.; Peterson, R. M.; Marchillo, K.; Andes, D.; Rajski, S. R.; Shen, B. Org. Lett. 2010, 12, 1744-1747
10. Zhang, C.; Ondeyka, J.; Herath, K.; Jayasuriya, H.; Guan, Z.; Zink, D. L.; Dietrich, L.; Burgess, B.; Ha, S. N.; Wang, J. J. Nat. Proc. 2011, 74, 329-340
11. Herath, K.; Attygalle, A. B.; Singh, S. B. Tetrahedron Lett. 2008, 49, 5755-5758
12. Syntheses of platencin: Nicolaou, K. C.; Tria, G. S.; Edmonds, D. J. Angew. Chem., Int. Ed. 2008, 47, 1780-1783
13. Hayashida, J.; Rawal, V. H. Angew. Chem., Int. Ed. 2008, 47, 4373-4376
14. Tiefenbacher, K.; Mulzer, J. Angew. Chem., Int. Ed. 2008, 47, 6199-6200
15. Yun, S. Y.; Zheng, J.-C.; Lee, D. Angew. Chem., Int. Ed. 2008, 47, 6201-6203
16. Waalboer, D. C. J.; Schaapman, M. C.; Van Delft, F. L.; Rutjes, F. P. J. T. Angew. Chem., Int. Ed. 2008, 47, 6576-6578
17. Nicolaou, K. C.; Toh, Q.-Y.; Chen, D. Y.-K. J. Am. Chem. Soc. 2008, 130, 11292-11293
18. addition/correction: J. Am. Chem. Soc. 2008, 130, 14016.
19. Austin, K. A. B.; Banwell, M. G.; Willis, A. C. Org. Lett. 2008, 10, 4465-4468
20. Tiefenbacher, K.; Mulzer, J. J. Org. Chem. 2009, 74, 2937-2941
21. Varseev, G. N.; Maier, M. E. Angew. Chem., Int. Ed. 2009, 48, 3685-3688
22. Ghosh, A. K.; Xi, K. Angew. Chem., Int. Ed. 2009, 48, 5372-5375
23. Nicolaou, K. C.; Tria, G. S.; Edmonds, D. J.; Kar, M. J. Am. Chem. Soc. 2009, 131, 15909-15917
24. Hirai, S.; Nakada, M. Tetrahedron Lett. 2010, 51, 5076-5079
25. Hirai, S.; Nakada, M. Tetrahedron 2011, 67, 518-530
26. Singh, V.; Sahu, B. C.; Bansal, V.; Mobin, S. M. Org. Biomol. Chem. 2010, 8, 4472-4481
27. Li, P.; Yamamoto, H. Chem. Commun. 2010, 46, 6294-6295
28. Wang, J.; Soisson, S. M.; Young, K.; Shoop, W.; Kodali, S.; Galgoci, A.; Painter, R.; Parthasarathy, G.; Tang, Y. S.; Cummings, R.; Ha, S.; Dorso, K.; Motyl, M.; Jayasuriya, H.; Ondeyka, J.; Herath, K.; Zhang, C.; Hernandez, L.; Allocco, J.; Basilio, A.; Tormo, J. R.; Genilloud, O.; Vicente, F.; Pelaez, F.; Colwell, L.; Lee, S. H.; Michael, B.; Felcetto, T.; Gill, C.; Silver, L. L.; Hermes, J. D.; Bartizal, K.; Barrett, J.; Schmatz, D.; Becker, J. W.; Cully, D.; Singh, S. B. Nature 2006, 441, 358-361
29. Singh, S. B.; Jayasuriya, H.; Ondeyka, J. G.; Herath, K. B.; Zhang, C.; Zink, D. L.; Tsou, N. N.; Ball, R. G.; Basilio, A.; Genilloud, O.; Diez, M. T.; Vicente, F.; Pelaez, F.; Young, K.; Wang, J. J. Am. Chem. Soc. 2006, 128, 11916-11920
30. addition/correction: J. Am. Chem. Soc. 2006, 128, 15547.
31. For reviews on fatty acid synthesis, see: Wright, H. T.; Reynolds, K. A. Curr. Opin. Microbiol. 2007, 10, 447-453
32. Goodman, C. D.; McFadden, G. I. Curr. Pharm. Des. 2008, 14, 901-916
33. Häebich, Dieter; von Nussbaum, F. Chem. Med. Chem. 2006, 1, 951-954
34. Johansson, P.; Wiltschi, B.; Kumari, P.; Kessler, B.; Vonrhein, C.; Vonck, J.; Oesterhelt, D.; Grininger, M. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 12803-12808
35. Selected papers on synthesis of platencin analogues: Barykina, O. V.; Rossi, K. L.; Rybak, M. J.; Snider, B. B. Org. Lett. 2009, 11, 5334-5337
36. Waalboer, D. C. J.; Leenders, S. H. A. M.; Schuelin-Casonato, T.; van Delft, F. L.; Rutjes, F. P. J. T. Chem.-Eur. J. 2010, 16, 11233-11236
37. Tiefenbacher, K.; Gollner, A.; Mulzer, J. Chem.-Eur. J. 2010, 16, 9616-9622
38. Leung, G. Y. C.; Li, H.; Toh, Q.-Y.; Ng, A. M.-Y.; Sum, R. J.; Bandow, J. E.; Chen, D. Y.-K. Eur. J. Org. Chem. 2011, 183-196
39. Nugent, W. A.; RajanBabu, T. V. J. Am. Chem. Soc. 1988, 110, 8561-8562
40. Green, M. L. H.; Lucas, C. R. J. Chem. Soc., Dalton Trans. 1972, 1000-1003
41. RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1989, 111, 4525-4527
42. For pertinent reviews, see: Barrero, A. F.; Quilez del Moral, J. F.; Sánchez, E. M.; Arteaga, J. F. Eur. J. Org. Chem. 2006, 1627-1641
43. Cuerva, J. M.; Justicia, J.; Oller-Lopez, J. L.; Oltra, J. E. Top. Curr. Chem. 2006, 264, 63-91
44. For some recent reports on Ti(III)-mediated cyclization of epoxides with alkenes, see: Mandal, S. K.; Paira, M.; Roy, S. C. J. Chem. Sci. 2010, 122, 423-426
45. Fernández-Mateos, A.; Madrazo, S. E.; Teijón, P. H.; González, R. R. J. Org. Chem. 2009, 74, 3913-3918
46. Mandal, S. K.; Paira, M.; Roy, S. C. J. Org. Chem. 2008, 73, 3823-3827
47. Chakraborty, T. K.; Samanta, R.; Das, S. J. Org. Chem. 2006, 71, 3321-3324
48. Toyota, M.; Wada, T.; Fukumoto, K.; Ihara, M. J. Am. Chem. Soc. 1998, 120, 4916-4925
49. Also see ref. For selected reviews, see: Nonhebel, D. C. Chem. Soc. Rev. 1993, 347-359
50. Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115
51. Bhosale, R. S.; Bhosale, S. V.; Bhosale, S. V.; Wang, T.; Zubaidha, P. K. Tetrahedron Lett. 2004, 45, 7187-7188
52. The pioneering work on 1,4-chiral induction of δ-hydroxyl acyclic esters, in which a tertiary stereocenter α to the ester carbonyl group is successfully created by δ-hydroxyl directed alkylation or aldolization, has been reported. Narasaka, K.; Ukaji, Y.; Watanabe, K. Bull. Chem. Soc., Jpn. 1987, 60, 1457-1464
53. Narasaka, K.; Ukaji, Y. Chem. Lett. 1986, 81-84
54. Narasaka, K.; Ukaji, Y.; Watanabe, K. Chem. Lett. 1986, 1755-1758
55. Metcalf, B. W.; Burkhart, J. P.; Jund, K. Tetrahedron Lett. 1980, 21, 35-36 either TBAF nor HF•Py, a common desilylating agent, gave the desired compound.
56. Nicolaou, K. C.; Gray, D. L. F.; Montagnon, T.; Harrison, S. T. Angew. Chem., Int. Ed. 2002, 41, 996-1000