A unified approach to ent -atisane diterpenes and related alkaloids: Synthesis of (-)-methyl atisenoate, (-)-isoatisine, and the hetidine skeleton

Journal of the American Chemical Society

Volumn 136, Issue 36, 2014, Pages 12592-12595

  Cherney, Emily C ^a   Lopchuk, Justin M ^a   Green, Jason C ^a   Baran, Phil S ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENES; UNIFIED APPROACH;

ATISINE; AZOMETHINE YLIDE; DITERPENE; HETIDINE; HETISINE; ISOATISINE; METHYL ATISENOATE; STEVIOL; UNCLASSIFIED DRUG; ALKALOID; KAURANE DERIVATIVE; OXAZOLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; HOFMANN LOFFLER FREYTAG REACTION; ISOMERIZATION; MUKAIYAMA REACTION; CHEMISTRY; CONFORMATION; SYNTHESIS;

ALKALOIDS; DITERPENES; DITERPENES, KAURANE; MOLECULAR CONFORMATION; OXAZOLES;

EID: 84907482061     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja507321j     Document Type: Article

References (42)

1. Hamlin, A. M.; Kisunzu, J. K.; Sarpong, R. Org. Biomol. Chem. 2014, 12, 1846
2. Cherney, E. C.; Baran, P. S. Isr. J. Chem. 2011, 51, 391 and references therein
3. Toyota, M.; Wada, T.; Fukumoto, K.; Ihara, M. J. Am. Chem. Soc. 1998, 120, 4916
4. Toyota, M.; Waka, T.; Ihara, M. J. Org. Chem. 2000, 65, 4565
5. Toyota, M.; Asano, T.; Ihara, M. Org. Lett. 2005, 7, 3929
6. Pelletier, S. W.; Jacobs, W. A. J. Am. Chem. Soc. 1956, 78, 4144
7. Pelletier, S. W.; Parthasarathy, P. C. Tetrahedron Lett. 1963, 4, 205
8. Nagata, W.; Sugasawa, T.; Narisada, M.; Wakabayashi, T.; Hayase, Y. J. Am. Chem. Soc. 1963, 85, 2342
9. Nagata, W.; Sugasawa, T.; Narisada, M.; Wakabayashi, T.; Hayase, Y. J. Am. Chem. Soc. 1967, 89, 1483
10. Ihara, M.; Suzuki, M.; Fukumoto, K.; Kametani, T.; Kabuto, C. J. Am. Chem. Soc. 1988, 110, 1963
11. Ihara, M.; Suzuki, M.; Fukumoto, K.; Kametani, T.; Kabuto, C. J. Am. Chem. Soc. 1990, 112, 1164
12. Liu, X.-Y.; Cheng, H.; Li, X.-H.; Chen, Q.-H.; Xu, L.; Wang, F.-P. Org. Biomol. Chem. 2012, 10, 1411
13. Hamlin, A. M.; Jesus-Cortez, F.; Lapointe, D.; Sarpong, R. Angew. Chem., Int. Ed. 2013, 52, 4854
14. Hamlin, A. M.; Lapointe, D.; Owens, K.; Sarpong, R. J. Org. Chem. 2014, 79, 6783
15. Muratake, H.; Natsume, M. Angew. Chem. 2004, 116, 4746
16. Peese, K. M.; Gin, D. Y. J. Am. Chem. Soc. 2006, 128, 8734
17. Peese, K. M.; Gin, D. Y. Chem.-Eur. J. 2008, 14, 1654
18. Yatsunami, T.; Isono, T.; Hayakawa, I.; Okamoto, T. Chem. Pharm. Bull. 1975, 3030
19. Yatsunami, T.; Furuya, S.; Okamoto, T. Chem. Pharm. Bull. 1978, 3199
20. Ishihara, Y.; Baran, P. S. Synlett 2010, 12, 1733
21. Chen, K.; Baran, P. S. Nature 2009, 459, 824
22. Jørgensen, L.; McKerrall, S. J.; Kuttruff, C. A.; Ungeheuer, F.; Felding, J.; Baran, P. S. Science 2013, 341, 878
23. Wilde, N. C.; Isomura, M.; Mendoza, A.; Baran, P. S. J. Am. Chem. Soc. 2014, 136, 4909
24. Cherney, E. C.; Green, J. C.; Baran, P. S. Angew. Chem., Int. Ed. 2013, 52, 9019
25. Gutekunst, W. R.; Baran, P. S. Chem. Soc. Rev. 2011, 40, 1976
26. Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960
27. Shibanuma, Y.; Okamoto, T. Chem. Pharm. Bull. 1985, 33, 3187
28. Francisco, C. G.; Herrera, A. J.; Suárez, E. J. Org. Chem. 2003, 68, 1012
29. Ogawa, T.; Nozaki, M.; Matsui, M. Tetrahedron 1980, 36, 2641
30. Isayama, S.; Mukaiyama, T. Chem. Lett. 1989, 1071
31. Gu, X.; Zhang, W.; Salomon, R. G. J. Org. Chem. 2012, 77, 1554
32. Ghisalberti, E. L.; Jefferies, P. R.; Mincham, W. A. Tetrahedron 1967, 23, 4463
33. 4 was isolated as a mixture of (-)-isoatisine and 19- epi -(-)-isoatisine. See: Reinecke, M. G.; Watson, W. H. J. Org. Chem. 1987, 52, 5051
34. Behrend, R. Justus Liebigs Ann. Chem. 1891, 265, 238
35. Smith, P. A. S.; Gloyer, S. E. J. Org. Chem. 1975, 40, 2504
36. Das, D.; Sun, A. X.; Seidel, D. Angew. Chem., Int. Ed. 2013, 52, 3765
37. Saidi, O.; Blacker, A. J.; Farah, M. M.; Marsden, S. P.; Williams, J. M. Angew. Chem., Int. Ed. 2009, 48, 7375
38. Escoubet, S.; Gastaldi, S.; Timokhin, V.; Bertrand, M.; Siri, D. J. Am. Chem. Soc. 2004, 126, 12343
39. Zhang, S.; He, G.; Zhao, Y.; Wright, K.; Nack, W. A.; Chen, G. J. Am. Chem. Soc. 2012, 134, 7313
40. Nadres, E. T.; Daugulis, O. J. Am. Chem. Soc. 2012, 134, 7
41. He, G.; Zhao, Y.; Zhang, S.; Lu, C.; Chen, G. J. Am. Chem. Soc. 2012, 134, 3
42. Ulubelen, A.; Desai, H. K.; Srivastava, S. K.; Hart, B. P.; Park, J. C.; Joshi, B. S.; Pelletier, W. J. Nat. Prod. 1996, 59, 360