Total synthesis of (±)-platencin

Angewandte Chemie - International Edition

Volumn 47, Issue 23, 2008, Pages 4373-4376

  Hayashida, Joji ^a   Rawal, Viresh H ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

Antibiotics; Cycloaddition; Natural products; Total synthesis

Indexed keywords

ACIDS; CHEMICAL REACTIONS;

ANTIBIOTICS; CYCLOADDITION; NATURAL PRODUCTS; TOTAL SYNTHESIS;

SYNTHESIS (CHEMICAL);

AMINOPHENOL DERIVATIVE; ANTIINFECTIVE AGENT; PLATENCIN; POLYCYCLIC HYDROCARBON;

ARTICLE; STEREOISOMERISM; SYNTHESIS; TECHNIQUE;

AMINOPHENOLS; ANTI-BACTERIAL AGENTS; METHODS; POLYCYCLIC COMPOUNDS; STEREOISOMERISM;

EID: 46749145371     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200800756     Document Type: Article

References (72)

1. M. Friedman, G. W. Friedland, Medicine's Ten Greatest Discoveries, Yale University Press, New Heaven, CT, 1998, pp. 263.
2. a) C. Walsh, Antibiotics: Actions, Origin, Resistance, ASM Press, Washington, DC, 2003;
3. b) S. B. Singh, J. F. Barrett, Biochem. Pharmacol. 2006, 71, 1006-1015.
4. a) C. Walsh, Nat. Rev. Microbiol. 2003, 1, 65-70;
5. b) C. H. T. Wright, K. A. Reynolds, Curr. Opin. Microbiol. 2007, 10, 447-453.
6. a) H. Jayasuriya, K. B. Herath, C. Zhang, D. L. Zink, A. Basilio, O. Genilloud, M. T. Diez, F. Vicente, I. Gonzalez, O. Salazar, F. Pelaez, R. Cummings, S. Ha, J. Wang, S. B. Singh, Angew. Chem. 2007, 119, 4768-4772;
7. Angew. Chem. Int. Ed. 2007, 46, 4684-4688;
8. b) J. Wang, S. Kodali, S. H. Lee, A. Galgoci, R. Painter, K. Dorso, F. Racine, M. Motyl, L. Hernandez, E. Tinney, S. L. Colletti, K. Herath, R. Cummings, O. Salazar, I. Gonzalez, A. Basilio, F. Vicente, O. Genilloud, F. Pelaez, H. Jayasuriya, K. Young, D. F. Cully, S. B. Singh, Proc. Natl. Acad. Sci. USA 2007, 104, 7612-7616.
9. a) J. Wang, S. M. Soisson, K. Young, W. Shoop, S. Kodali, A. Galgoci, R. Painter, G. Parthasarathy, Y. S. Tang, R. Cummings, S. Ha, K. Dorso, M. Motyl, H. Jayasuriya, J. Ondeyka, K. Herath, C. Zhang, L. Hernandez, J. Allocco, A. Basilio, J. R. Tormo, O. Genilloud, F. Vicente, F. Pelaez, L. Colwell, S. H. Lee, B. Michael, T. Felcetto, C. Gill, L. L. Silver, J. D. Hermes, K. Bartizal, J. Barrett, D. Schmatz, J. W. Becker, D. Cully, S. B. Singh, Nature 2006, 441, 358-361;
10. b) S. B. Singh, H. Jayasuriya, J. G. Ondeyka, K. B. Herath, C. Zhang, D. L. Zink, N. N. Tsou, R. G. Ball, A. Basilio, O. Genilloud, M. T. Diez, F. Vicente, F. Pelaez, K. Young, J. Wang, J. Am. Chem. Soc. 2006, 128, 11916-11920;
11. c) S. B. Singh, K. B. Herath, J. Wang, N. Tsou, R. G. Ball, Tetrahedron Lett. 2007, 48, 5429-5433;
12. d) K. B. Herath, A. B. Attygalle, S. B. Singh, J. Am. Chem. Soc. 2007, 129, 15422-15423.
13. a) K. C. Nicolaou, A. Li, D. J. Edmonds, Angew. Chem. 2006, 118, 7244-7248;
14. Angew. Chem. Int. Ed. 2006, 45, 7086-7090;
15. b) K. C. Nicolaou, Y. Tang, J. Wang, Chem. Commun. 2007, 1922-1923;
16. c) K. C. Nicolaou, D. J. Edmonds, A. Li, G. S. Tria, Angew. Chem. 2007, 119, 4016-4019;
17. Angew. Chem. Int. Ed. 2007, 46, 3942-3945;
18. d) Y. Zou, C. Chen, C. D. Taylor, B. M. Foxman, B. B. Snider, Org. Lett. 2007, 9, 1825-1828;
19. e) K. P. Kaliappan, V. Ravikumar, Org. Lett. 2007, 9, 2417-2419;
20. f) P. Li, J. N. Payette, H. Yamamoto, J. Am. Chem. Soc. 2007, 129, 9534-9535;
21. g) K. Tiefenbacher, J. Mulzer Angew. Chem. 2007, 119, 8220-8221;
22. Angew. Chem. Int. Ed. 2007, 46, 8074-8075;
23. Angew. Chem. Int. Ed. 2007, 46, 8074-8075;
24. h) A. K. Ghosh, K. Xi, Org. Lett. 2007, 9, 4013-4016;
25. i) G. Lalic, E. J. Corey, Org. Lett. 2007, 9, 4921-4923;
26. j) P. Heretsch, A. Giannis, Synthesis 2007, 2614-2616;
27. k) K. C. Nicolaou, D. Pappo, K. Y. Tsang, R. Gibe, D. Y. Chen, Angew. Chem. 2008, 120, 958-960;
28. Angew. Chem. Int. Ed. 2008, 47, 944-946;
29. l) K. Tiefenbacher, J. Mulzer, Angew. Chem. 2008, 120, 2582-2590;
30. Angew. Chem. Int. Ed. 2008, 47, 2548-2555.
31. Studies on synthetic analogues of platensimycin: a) K. C. Nicolaou, T. Lister, R. M. Denton, A. Montero, D. J. Edmonds, Angew. Chem. 2007, 119, 4796-4798;
32. Angew. Chem. Int. Ed. 2007, 46, 4712-4714;
33. b) K. C. Nicolaou, Y. Tang, J. Wang, A. F. Stepan, A. Li, A. Montero, J. Am. Chem. Soc. 2007, 129, 14850-14851.
34. As this manuscript was being prepared for submission, the first total synthesis of platencin was reported: K. C. Nicolaou, G. S. Tria, D. J. Edmonds, Angew. Chem. 2008, 120, 1804-1807;
35. Angew. Chem. Int. Ed. 2008, 47, 1780-1783.
36. a) D. F. Taber, J. Org. Chem. 1976, 41, 2649-2650;
37. b) D. F. Taber, B. P. Gunn, I.-C. Chiu, Org. Synth. 1983, 61, 59-61.
38. a) S. Danishefsky, T. Kitahara, C. F. Yan, J. Morris, J. Am. Chem. Soc. 1979, 101, 6996-7000;
39. b) F. Fringuelli, F. Pizzo, A. Taticchi, E. Wenkert, J. Org. Chem. 1983, 48, 2802-2808;
40. c) M. Ge, B. M. Stoltz, E. J. Corey, Org. Lett. 2000, 2, 1927-1929;
41. d) A. Gagnon, S. J. Danishefsky, Angew. Chem. 2002, 114, 1651-1654;
42. Angew. Chem. Int. Ed. 2002, 41, 1581-1584;
43. e) M. E. Jung, D. Ho, H. V. Chu, Org. Lett. 2005, 7, 1649-1651;
44. f) S.-J. Min, G. O. Jones, K. N. Houk, S. J. Danishefsky, J. Am. Chem. Soc. 2007, 129, 10078-10079.
45. a) S. A. Kozmin, V. H. Rawal, J. Org. Chem. 1997, 62, 5252-5253;
46. b) S. A. Kozmin, J. M. Janey, V. H. Rawal, J. Org. Chem. 1999, 64, 3039-3052;
47. c) S. A. Kozmin, V. H. Rawal, J. Am. Chem. Soc. 1999, 121, 9562-9573;
48. d) J. Renaud, C. Aubert, M. Malacria, Tetrahedron Lett. 1999, 40, 5015-5018;
49. e) P. P. Seth, N. I. Totah, Org. Lett. 1999, 1, 1411-1414;
50. f) R. Paczkowski, C. Maichle-Mossmer, M. E. Maier, Org. Lett. 2000, 2, 3967-3969;
51. g) T. L. S. Kishbaugh, G. W. Gribble, Tetrahedron Lett. 2001, 42, 4783-4785;
52. h) Y. Huang, V. H. Rawal, J. Am. Chem. Soc. 2002, 124, 9662-9663;
53. i) Y. Huang, V. H. Rawal, Org. Lett. 2000, 2, 3321-3323;
54. j) R. Kawȩcki, Tetrahedron: Asymmetry 2006, 17, 1420-1423;
55. k) A. B. Smith, K. Basu, T. Bosanac, J. Am. Chem. Soc. 2007, 129, 14872-14874.
56. a) D. Sole, Y. Cancho, A. Llebaria, J. M. Moreto, A. Delgado, J. Am. Chem. Soc. 1994, 116, 12133-12134;
57. b) D. Sole, J. Bonjoch, J. Bosch, J. Org. Chem. 1996, 61, 4194-4195.
58. a) D. Sole, J. Bonjoch, J. Bosch, J. Org. Chem. 1996, 61, 4194-4195;
59. b) K. C. Nicolaou, A. J. Roecker, M. Follmann, R. Baati, Angew. Chem. 2002, 114, 2211-2214;
60. Angew. Chem. Int. Ed. 2002, 41, 2107-2110.
61. The cod was added to make up for any that might escape during the reaction and thereby prevent degradation of the highly reactive nickel species during the reaction.
62. L. Caglioti, M. Magi, Tetrahedron 1963, 19, 1127-1131.
63. (E)-1-Tribenzylsilyl-3-iodo-prop-1-ene was prepared from propargyl alcohol in two steps, see the Supporting Information.
64. a) K. Tamao, N. Ishida, T. Tanaka, M. Kumada, Organometallics 1983, 2, 1694-1696;
65. b) K. Tamao, M. Kumada, K. Maeda, Tetrahedron Lett. 1984, 25, 321-324;
66. c) I. Fleming, R. Henning, H. Plaut, J. Chem. Soc. Chem. Commun. 1984, 29-31.
67. The role of iodosobenzene in this reaction is under investigation, and the details will be reported in due course.
68. The chlorite oxidation of aldehydes has been referred to in the literature as the Pinnick oxidation. However, in his report on the oxidation of α,β-unsaturated aldehydes, Professor Pinnick credits Lindgren and Kraus for the key developments of this reaction; see: a) B. O. Lindgren, T. Nilsson, Acta Chem. Scand. 1973, 27, 888-890;
69. b) G. A. Kraus, M. J. Taschner, J. Org. Chem. 1980, 45, 1175-1176;
70. c) G. A. Kraus, B. Roth, J. Org. Chem. 1980, 45, 4825-4830;
71. d) B. S. Bal, W. E. Childers, H. W. Pinnick, Tetrahedron 1981, 37, 2091-2096.
72. 3-Amino-2,4-dihydroxybenzoic acid 13 was prepared from 2,4-dihydroxybenzoic acid in four steps, see the Supporting Information.