Bioinspired total synthesis of bolivianine: A diels-alder/intramolecular hetero-Diels-Alder cascade approach

Journal of the American Chemical Society

Volumn 135, Issue 25, 2013, Pages 9291-9294

  Yuan, Changchun ^a   Du, Biao ^a   Yang, Li ^a   Liu, Bo ^a,b  

^a China   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATION; HETERO-DIELS-ALDER; INTRAMOLECULAR CYCLOPROPANATIONS; METAL CARBENES; PALLADIUM-CATALYZED; SINGLE-STEP; SYNTHESIS FEATURES; TOTAL SYNTHESIS;

CHEMISTRY;

SYNTHESIS (CHEMICAL);

BOLIVANINE; NATURAL PRODUCT; SPINOSYN A; UNCLASSIFIED DRUG;

ARTICLE; BIOGENESIS; CONFORMATION; CYCLOADDITION; CYCLOPROPANATION; DIASTEREOISOMER; DIELS ALDER REACTION; EPOXIDATION; MICHAEL ADDITION; SYNTHESIS;

MOLECULAR CONFORMATION; SESQUITERPENES; TERPENES;

EID: 84879510518     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja4040335     Document Type: Article

References (53)

1. Acebey, L.; Sauvain, M.; Beck, S.; Moulis, C.; Gimenez, A.; Jullian, V. Org. Lett. 2007, 9, 4693
2. Acebey, L.; Jullian, V.; Sereno, D.; Chevalley, S.; Estevez, Y.; Moulis, C.; Beck, S.; Valentin, A.; Gimenez, A.; Sauvain, M. Planta Med. 2010, 76, 365
3. Trentin, A. P.; Santos, A. R. S.; Guedes, A.; Pizzolatti, M. G.; Yunes, R. A.; Calixto, J. B. Planta Med. 1999, 65, 517
4. Bohlmann, F.; Zdero, C.; King, R. M.; Robinson, H. Phytochemistry 1980, 19, 689
5. Shimada, T.; Endo, T.; Fujii, H.; Hara, M.; Omura, M. Plant Sci. 2005, 168, 987
6. Dudareva, N.; Martin, D.; Kish, C. M.; Kolosova, N.; Gorenstein, N.; Faldt, J.; Miller, B.; Bohlmann, J. Plant Cell 2003, 15, 1227
7. Lorenzo, D.; Loayza, I.; Dellacassa, E. Flavour Fragr. J. 2003, 18, 32
8. Zhan, Z.-J.; Ying, Y.-M.; Ma, L.-F.; Shan, W.-G. Nat. Prod. Rep. 2011, 28, 594
9. Kim, H. J.; Ruszczycky, M. W.; Choi, S.; Liu, Y.; Liu, H. Nature 2011, 473, 109
10. Hess, B. A., Jr.; Smentek, L. Org. Biomol. Chem. 2012, 10, 7503
11. Takao, K.; Munakata, R.; Tadano, K. Chem. Rev. 2005, 105, 4779
12. Stocking, E. M.; Williams, R. M. Angew. Chem., Int. Ed. 2003, 42, 3078
13. Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668
14. Li, C.; Dong, T.; Dian, L.; Zhang, W.; Lei, X. Chem. Sci. 2013, 4, 1163
15. Li, C.; Dian, L.; Zhang, W.; Lei, X. J. Am. Chem. Soc. 2012, 134, 12414
16. Peng, F.; Danishefsky, S. J. J. Am. Chem. Soc. 2012, 134, 18860
17. Evans, D. A.; Adams, D. J.; Kwan, E. E. J. Am. Chem. Soc. 2012, 134, 8162
18. Deng, J.; Zhu, B.; Lu, Z.; Yu, H.; Li, A. J. Am. Chem. Soc. 2012, 134, 920
19. Snyder, S. A.; Wespe, D. A.; von Hof, J. M. J. Am. Chem. Soc. 2011, 133, 8850
20. Petronijevic, F. R.; Wipf, P. J. Am. Chem. Soc. 2011, 133, 7704
21. Herzon, S. B.; Calandra, N. A.; King, S. M. Angew. Chem., Int. Ed. 2011, 50, 8863
22. Xiao, Q.; Ren, W.-W.; Chen, Z.-X.; Sun, T.-W.; Li, Y.; Ye, Q.-D.; Gong, J.-X.; Meng, F.-K.; You, L.; Liu, Y.-F. Angew. Chem., Int. Ed. 2011, 50, 7373
23. Gong, J.-X.; Lin, G.; Sun, W.-B.; Li, C.-C.; Yang, Z. J. Am. Chem. Soc. 2010, 132, 16745
24. Liu, L.-Z.; Han, J.-C.; Yue, G.-Z.; Li, C.-C.; Yang, Z. J. Am. Chem. Soc. 2010, 132, 13608
25. Sasaki, Y.; Kato, D.; Boger, D. L. J. Am. Chem. Soc. 2010, 132, 13533
26. Roush, W. R.; Sciotti, R. J. J. Am. Chem. Soc. 1998, 120, 7411
27. The methyl ether of 10 is linderoxide, a natural sesquiterpenoid, which suggests biosynthetic connections among 2, 10, and linderoxide. For the isolation of linderoxide, see: Ishii, H.; Tozyo, T.; Nakamura, M.; Takeda, K. Tetrahedron 1968, 24, 625
28. Yue, G.; Yang, L.; Yuan, C.; Du, B.; Liu, B. Tetrahedron 2012, 68, 9624
29. Yue, G.; Yang, L.; Yuan, C.; Jiang, X.; Liu, B. Org. Lett. 2011, 13, 5406
30. Watanabe, M.; Awen, B. Z.; Kato, M. J. Org. Chem. 1993, 58, 3923
31. Maas, G. Angew Chem., Int. Ed. 2009, 48, 8186
32. Fulton, J. R.; Aggarwal, V. K.; Vicente, J. Eur. J. Org. Chem. 2005, 1479
33. Barluenga, J.; Quinones, N.; Tomas-Gamasa, M.; Cabal, M.-P. Eur. J. Org. Chem. 2012, 2312
34. Zhang, J.-L.; Chan, P. W. H.; Che, C.-M. Tetrahedron Lett. 2003, 44, 8733
35. de Meijere, A.; Schulz, T.-J.; Kostikov, R. R.; Graupner, F.; Murr, T.; Bielfeldt, T. Synthesis 1991, 547
36. Niu, D.; Hoye, T. R. Org. Lett. 2012, 14, 828
37. Couladouros, E. A.; Bouzas, E. A.; Magos, A. D. Tetrahedron 2006, 62, 5272
38. Zapf, C. W.; Harrison, B. A.; Drahl, C.; Sorensen, E. J. Angew. Chem., Int. Ed. 2005, 44, 6533
39. Snider, B. B.; Zou, Y. Org. Lett. 2005, 7, 4939
40. Uenishi, J.; Kawahama, R.; Yonemitsu, O. J. Org. Chem. 1997, 62, 1691
41. Takeda, K.; Igarashi, Y.; Okazaki, K.; Yoshii, E.; Yamaguchi, K. J. Org. Chem. 1990, 55, 3431
42. Alonso, D.; Orti, J.; Branchadell, V.; Oliva, A.; Ortuno, R. M.; Bertran, J.; Font, J. J. Org. Chem. 1990, 55, 3060
43. Dubios, S.; Rodier, F.; Blanc, R.; Rahmani, R.; Heran, V.; Thibonnet, J.; Commeiras, L.; Parrain, J.-L. Org. Biomol. Chem. 2012, 10, 4712
44. Takeda, K.; Yano, S.; Sato, M.; Yoshii, E. J. Org. Chem. 1987, 52, 4135
45. Branchadell, V.; Font, J.; Oliva, A.; Orti, J.; Ortuno, R. M. Tetrahedron 1991, 47, 8775
46. Poss, A. J.; Brodowski, M. H. Tetrahedron Lett. 1989, 30, 2505
47. For preparation of β- E -ocimene, see: Cong, H.; Becker, C. F.; Elliott, S. J.; Grinstaff, M. W.; Porco, J. A., Jr. J. Am. Chem. Soc. 2010, 132, 7514
48. Majetich, G.; Zhang, Y. J. Am. Chem. Soc. 1994, 116, 4979
49. For the thermal stability of β- E -ocimene, see: Wolinsky, J.; Chollar, B.; Baird, M. D. J. Am. Chem. Soc. 1962, 84, 2775
50. Tanaka, N.; Suzuki, T.; Matsumura, T.; Hosoya, Y.; Nakada, M. Angew. Chem., Int. Ed. 2009, 48, 2580
51. Evans, D. A.; Starr, J. T. J. Am. Chem. Soc. 2003, 125, 13531
52. Vanderwal, C. D.; Vosburg, D. A.; Weiler, S.; Sorensen, E. J. J. Am. Chem. Soc. 2003, 125, 5393
53. For the preparation of 30, see: Varseev, G. N.; Maier, M. E. Org. Lett. 2007, 9, 1461