Stereocontrolled formal synthesis of (±)-platensimycin

Organic Letters

Volumn 10, Issue 18, 2008, Pages 4049-4052

  Matsuo, Jun Ichi ^a   Takeuchi, Kosuke ^a   Ishibashi, Hiroyuki ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADAMANTANE; AMINOBENZOIC ACID DERIVATIVE; ANILIDE; PLATENSIMYCIN;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ADAMANTANE; AMINOBENZOIC ACIDS; ANILIDES; CATALYSIS; CYCLIZATION; STEREOISOMERISM;

EID: 55949084611     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801584r     Document Type: Article

References (50)

1. (a) Wang, J.; Soisson, S. M.; Young, K.; Snoop, 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, S. B.; Barrett, J.; Schmatz, D.; Becker, J. W.; Cully, D.; Singh, S. B. Nature 2006, 441, 358.
2. (b) 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.; Vincente, F.; Pelaez, F.; Young, K.; Wang, J. J. Am. Chem. Soc. 2006, 128, 11916.
3. (a) Nicolaou, K. C.; Li, A.; Edmonds, D. J. Angew. Chem., Int. Ed. 2006, 45, 7086.
4. (b) Nicolaou, K. C.; Edmonds, D. J.; Li, A.; Tria, G. S. Angew. Chem., Int. Ed. 2007, 46, 3942.
5. (c) Li, P.; Fayette, J. N.; Yamamoto, H. J. Am. Chem. Soc. 2007, 129, 9534.
6. (d) Lalic, G.; Corey, E. J. Org. Lett. 2007, 9, 4921.
7. (e) Nicolaou, K. C.; Pappo, D.; Tsung, K. Y.; Gibe, R.; Chen, D. Y.-K. Angew. Chem., Int. Ed. 2008, 47, 944.
8. (f) Kim, C. H.; Jang, K. P.; Choi, S. Y.; Chung, Y. K.; Lee, E. Angew. Chem., Int. Ed. 2008, 47, 4009.
9. (g) Zou, Y.; Chen, C.-H.; Taylor, C. D.; Foxman, B. M.; Snider, B. B. Org. Lett. 2007, 9, 1825.
10. (h) Nicolaou, K. C.; Tang, Y.; Wang, J. Chem. Commun. 2007, 1922.
11. (i) Tiefenbacher, K.; Mulzer, J. Angew. Chem., Int. Ed 2007, 46, 8074.
12. (j) Tiefenbacher, K.; Mulzer, J. Angew. Chem., Int. Ed. 2008, 47, 2548.
13. Total synthesis of platencin, a platensimycin analogue: (a) Nicolaou, K. C.; Tria, G. S.; Edmonds, D. J. Angew. Chem., Int. Ed 2008, 47, 1780.
14. (b) Hayashida, J.; Rawal, V. H. Angew. Chem., Int. Ed. 2008, 47, 4373.
15. (c) Tiefenbacher, K.; Mulzer, J. Angew. Chem., Int. Ed. 2008, 47, 6199.
16. (d) Yun, S. Y.; Zheng, J.-C.; Lee, D. Angew. Chem., Int. Ed. 2008, 47, 6201.
17. Transannular cyclization of cyclooct-4-enyl radical: (a) Dowbenko, R. J. Am. Chem. Soc. 1964, 86, 946.
18. (b) Dowbenko, R. Tetrahedron 1964, 20, 1843.
19. (c) Friedman, L. J. Am. Chem. Soc. 1964, 86, 1885.
20. (d) Gancarz, R. A.; Kice, J. J. J. Org. Chem. 1981, 46, 4899.
21. (e) Winkler, J. D.; Sridar, V. J. Am. Chem. Soc. 1986, 108, 1708.
22. (a) Rawal, V. H.; Singh, S. P.; Dufour, C.; Michoud, C. J. Org. Chem. 1991, 56, 5245.
23. (b) Mesmaeker, A. D.; Waldner, A.; Hoffmann, P.; Mindt, T.; Hug, P.; Winkler, T. Synlett 1990, 687.
24. Danishefsky, S.; Kitahara, T. J. Am. Chem. Soc. 1974, 96, 7807.
25. Frantz, D. E.; Singleton, D. A. Org. Lett. 1999, 1, 485.
26. Sharpless, K. B.; Michaelson, R. C. J. Am. Chem. Soc. 1973, 95, 6136.
27. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
28. Isomerization of β,γ-epoxycyclohexanones: Delay, F.; Ohloff, G. Helv. Chim. Acta 1979, 62, 2168.
29. Mancuso, A. J.; Swern, D. Synthesis 1981, 165.
30. (a) Corey, E. J.; Schmidt, G. Tetrahedron Lett. 1979, 399.
31. (b) Herscovici, J.; Egron, M.-J.; Antonakis, K. J. Chem. Soc., Perkin Trans. I 1982, 1967.
32. Some examples for the Diels-Alder reaction between 2-alkyl-2-cyclohexen- 1-ones and 13a: (a) Danishefsky, S.; Kitahara, T. J. Org. Chem. 1975, 40, 538.
33. (b) Inokuchi, T.; Okano, M.; Miyamoto, T.; Madon, H. B.; Takagi, M. Synlett 2000, 1549.
34. Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357.
35. (a) Smith, A. B.; Cho, Y. S.; Friestad, G. K. Tetrahedron Lett. 1998, 39, 8765.
36. (b) Hosokawa, T.; Hirata, M.; Murahashi, S.-I.; Sonoda, A. Tetrahedron Lett. 1976, 1821.
37. Semmelhack, M. F.; Kim, C. R.; Dobler, W.; Meier, M. Tetrahedron Lett. 1989, 30, 4925.
38. (a) Comins, D. L.; Dehghani, A.; Foti, C. J.; Joseph, S. P. Org. Synth. 1997, 74, 77.
39. (b) Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299.
40. Cacchi, S.; Morera, E.; Ortar, G. Tetrahedron Lett. 1984, 25, 4821.
41. Scott, W. J.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630.
42. When the addition of benzenethiol to the alkenyl ether moiety was carried out by employing a catalytic amount of PPTS, deprotection of the acetal group of 19 also took place.
43. Reductive radical cyclization of monothioacetal: (a) Yadav, V. K.; Fallis, A. G. Tetrahedron Lett. 1988, 29, 897.
44. (b) Sato, K.; Sasaki, M. Org. Lett. 2005, 7, 2441.
45. Reaction of 1-alkoxyalkyl radicals from selenoacetal: (a) Rawal, V. H.; Singh, S. P.; Dufour, C.; Michoud, C. J. Org. Chem. 1991, 56, 5245.
46. (b) Mesmaeker, A. D.; Waldner, A.; Hoffmann, P.; Mindt, T.; Hug, P.; Winkler, T. Synlett 1990, 687.
47. (c) Nishiyama, Y.; Yamamoto, H.; Nakata, S.; Ishii, Y. Chem. Lett. 1993, 841.
48. Braga, A. L.; Silveira, C. C.; Zeni, G.; Severe Filho, W. A.; Stefani, H. A. J. Chem. Res. (S) 1996, 206.
49. Lee, J. S.; Fuchs, P. L. Org. Lett. 2003, 5, 2247.
50. Singh, S. B.; Herath, K. B.; Wang, J.; Tsou, N.; Ball, R. G. Tetrahedron Lett. 2007, 48, 5429.