A Biomimetic Synthesis of Phaitanthrin e Involving a Fragmentation of sp3 Carbon-Carbon Bond: Synthesis and Rearrangement of Phaitanthrin D to Phaitanthrin e

Organic Letters

Volumn 17, Issue 24, 2015, Pages 6218-6221

  Vaidya, Sagar D ^a   Argade, Narshinha P ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; PHAITANTHRIN D; PHAITANTHRIN E; QUINAZOLINONE DERIVATIVE;

BIOMIMETICS; CHEMICAL STRUCTURE; CHEMISTRY; ORCHIDACEAE; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; BIOMIMETICS; MOLECULAR STRUCTURE; ORCHIDACEAE; QUINAZOLINONES; STEREOISOMERISM;

EID: 84952684740     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b03203     Document Type: Article

References (32)

1. Mhaske, S. B.; Argade, N. P. Tetrahedron 2006, 62, 9787 10.1016/j.tet.2006.07.098
2. Kshirsagar, U. A. Org. Biomol. Chem. 2015, 13, 9336 10.1039/C5OB01379H
3. Jao, C. W.; Lin, W. C.; Wu, Y. T.; Wu, P. L. J. Nat. Prod. 2008, 71, 1275 10.1021/np800064w
4. Wessjohann, L. A.; Brandt, W.; Thiemann, T. Chem. Rev. 2003, 103, 1625 10.1021/cr0100188
5. Borthwick, A. D. Chem. Rev. 2012, 112, 3641 10.1021/cr200398y
6. Westheimer, F. H. Science 1987, 235, 1173 10.1126/science.2434996
7. Butler, A.; Sandy, M. Nature 2009, 460, 848 10.1038/nature08303
8. Newhouse, T.; Lewis, C. A.; Eastman, K. J.; Baran, P. S. J. Am. Chem. Soc. 2010, 132, 7119 10.1021/ja1009458
9. Kim, J.; Movassaghi, M. J. Am. Chem. Soc. 2011, 133, 14940 10.1021/ja206743v
10. Hu, B.-Q.; Wang, L.-X.; Yang, L.; Xiang, J.-F.; Tang, Y.-L. Eur. J. Org. Chem. 2015, 2015, 4504 10.1002/ejoc.201500473
11. Mohammed, S.; Vishwakarma, R. A.; Bharate, S. B. J. Org. Chem. 2015, 80, 6915 10.1021/acs.joc.5b00989
12. Drahl, M. A.; Manpadi, M.; Williams, L. J. Angew. Chem., Int. Ed. 2013, 52, 11222 10.1002/anie.201209833
13. Mahoney, S. J.; Lou, T.; Bondarenko, G.; Fillion, E. Org. Lett. 2012, 14, 3474 10.1021/ol301442z
14. Cordaro, J. G.; Bergman, R. G. J. Am. Chem. Soc. 2004, 126, 3432 10.1021/ja031784u
15. Anand, R. C.; Milhotra, A. Chem. Commun. 1999, 15, 1415 10.1039/a903959g
16. Krapcho, A. P.; Glynn, G. A.; Grenon, B. J. Tetrahedron Lett. 1967, 8, 215 10.1016/S0040-4039(00)90519-7
17. Vaidya, S. D.; Argade, N. P. Org. Lett. 2013, 15, 4006 10.1021/ol4018062
18. Kshirsagar, U. A.; Argade, N. P. Org. Lett. 2010, 12, 3716 10.1021/ol101597p
19. Kshirsagar, U. A.; Puranik, V. G.; Argade, N. P. J. Org. Chem. 2010, 75, 2702 10.1021/jo100400z
20. Souillart, L.; Cramer, N. Chem. Rev. 2015, 115, 9410 10.1021/acs.chemrev.5b00138
21. Chen, Y.-C.; Zhu, M.-K.; Loh, T.-P. Org. Lett. 2015, 17, 2712 10.1021/acs.orglett.5b01127
22. Yada, A.; Fujita, S.; Murakami, M. J. Am. Chem. Soc. 2014, 136, 7217 10.1021/ja502229c
23. Chen, F.; Wang, T.; Jiao, N. Chem. Rev. 2014, 114, 8613 10.1021/cr400628s
24. Murphy, G. K.; Hama, N.; Bedermann, A.; Dong, P.; Schneider, C. M.; McMahon, T. C.; Tao, R. N.; Twenter, B. M.; Spiegel, D. A.; Wood, J. L. Org. Lett. 2012, 14, 4544 10.1021/ol302011b
25. Cai, S.; Zhao, X.; Wang, X.; Liu, Q.; Li, Z.; Wang, D. Z. Angew. Chem., Int. Ed. 2012, 51, 8050 10.1002/anie.201202880
26. Youn, S. W.; Kim, B. S.; Jagdale, A. R. J. Am. Chem. Soc. 2012, 134, 11308 10.1021/ja304616q
27. Ishida, N.; Sawano, S.; Masuda, Y.; Murakami, M. J. Am. Chem. Soc. 2012, 134, 17502 10.1021/ja309013a
28. Dreis, A. M.; Douglas, C. J. J. Am. Chem. Soc. 2009, 131, 412 10.1021/ja8066308
29. Jun, C.-H. Chem. Soc. Rev. 2004, 33, 610 10.1039/b308864m
30. Kang, G.; Luo, Z.; Liu, C.; Gao, H.; Wu, Q.; Wu, H.; Jiang, J. Org. Lett. 2013, 15, 4738 10.1021/ol402104p
31. Gao, H.; Luo, Z.; Ge, P.; He, J.; Zhou, F.; Zheng, P.; Jiang, J. Org. Lett. 2015, 17, ASAP, DOI: 10.1021/acs.orglett.5b02891.
32. Kshirsagar, U. A.; Mhaske, S. B.; Argade, N. P. Tetrahedron Lett. 2007, 48, 3243 10.1016/j.tetlet.2007.03.032