Stereocontrolled synthesis of the tricyclic ABC ring system of daphnicyclidin A

Organic Letters

Volumn 16, Issue 7, 2014, Pages 1956-1959

  Williams, David R ^a   Mondal, Prolay K ^a   Bawel, Seth A ^a   Nag, Partha P ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; DAPHNICYCLIDIN A;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SAXIFRAGACEAE; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; CYCLIZATION; MOLECULAR STRUCTURE; SAXIFRAGACEAE; STEREOISOMERISM;

EID: 84898761686     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol5005092     Document Type: Article

References (46)

1. Dong, M.; Zhang, M.-L.; Shi, Q.-W.; Gu, Y.-C.; Kiyota, H. Curr. Org. Chem. 2009, 13, 646-682
2. Kobayashi, J.; Kubota, T. Nat. Prod. Rep. 2009, 26, 936-962
3. Kobayashi, J.; Morita, H. The Daphniphyllum Alkaloids. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 2003; Vol. 60, Chapter 3, pp 165-205.
4. Kobayashi, J.; Inaba, Y.; Shiro, M.; Yoshida, N.; Morita, H. J. Am. Chem. Soc. 2001, 123, 11402-11408
5. Morita, H.; Yoshida, N.; Kobayashi, J. J. Org. Chem. 2002, 67, 2278-2282
6. Gan, X. W.; Bai, H. Y.; Chen, Q. G.; Ma, L.; Hu, L. H. Chem. Biodiversity 2006, 3, 1255-1259
7. Zhang, Y.; He, H.; Di, Y.; Mu, S.; Wang, Y.; Wang, J.; Li, C.; Kong, N.; Gao, S.; Hao, X. Tetrahedron Lett. 2007, 48, 9104-9107
8. Zhang, Y.; Di, Y.-T..; Liu, H.-Y.; Li, C.-S.; Tan, C.-J.; Zhang, Q.; Fang, X.; Li, S.-L.; Hao, X.-J. Helv. Chim. Acta 2008, 91, 2153-2158
9. Yang, S. P.; Yue, J. M. Org. Lett. 2004, 6, 1401-1404
10. Yang, S. P.; Yue, J. M. Helv. Chim. Acta 2006, 89, 2783-2788
11. Jossang, A.; El Bitar, H.; Pham, V. C.; Sevenet, T. J. Org. Chem. 2003, 68, 300-304
12. Chen, X.; Zhan, Z. J.; Yue, J. M. Helv. Chim. Acta 2005, 88, 854-860
13. Yang, S. P.; Yue, J. M. Org. Lett. 2004, 6, 1401-1404
14. Dunn, T. B.; Ellis, J. M.; Kofink, C. C.; Manning, J. R.; Overman, L. E. Org. Lett. 2009, 11, 5658-5661
15. Ikeda, S.; Shibuya, M.; Kanoh, N.; Iwabuchi, Y. Org. Lett. 2009, 11, 1833-1836
16. Lu, Z.; Li, Y.; Deng, J.; Li, A. Nature Chem. 2013, 5, 679-684
17. Weiss, M. E.; Carreira, E. M. Angew. Chem., Int. Ed. 2011, 50, 11501-11505
18. Xu, C.; Wang, L.; Hao, X.; Wang, D. Z. J. Org. Chem. 2012, 77, 6307-6313
19. Ibrahim, A. A.; Golonka, A. N.; Lopez, A. M.; Stockdill, J. L. Org. Lett. 2014, 16, 1072-1075
20. Wang, L.; Xu, C.; Chen, L.; Hao, X.; Wang, D. Z. Org. Lett. 2014, 16, 1076-1079
21. Williams, D. R.; Reeves, J. T.; Nag, P. P.; Pitcock, W. H., Jr.; Baik, M.-H. J. Am. Chem. Soc. 2006, 128, 12339-12348
22. Doboudin, J. G.; Jousseaume, B.; Bonakdar, A. J. Organomet. Chem. 1979, 168, 227-232
23. Marshall, J. A.; Bartley, G. S.; Wallace, E. M. J. Org. Chem. 1996, 61, 5729-5735
24. Silva, F.; Sawicki, M.; Gouverneur, V. Org. Lett. 2006, 8, 5417-5419
25. Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986-2012
26. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519
27. Hoye, T. R.; Jeffrey, C. S.; Shao, F. Nat. Protoc. 2007, 2, 2451-2458
28. 3N; MeOH; 83%), protection with tert -butyldiphenylsilyl chloride and imidazole (96%), and hydrolysis (LiOH; aqueous THF). For related efforts, see: Toshima, H.; Aramaki, H.; Ichihara, A. Tetrahedron Lett. 1999, 40, 3587-3590
29. For NOESY correlations of similar butyrolactones, see: Williams, D. R.; Walsh, M. J.; Miller, N. A. J. Am. Chem. Soc. 2009, 131, 9038-9045
30. Sajiki, H.; Hattori, K.; Hirota, K. J. Org. Chem. 1998, 63, 7990-7992
31. Kan, T.; Kobayashi, H.; Fukuyama, T. Synlett 2002, 5, 697-699
32. Sakaguchi, H.; Tokuyama, H.; Fukuyama, T. Org. Lett. 2007, 9, 1635-1638
33. Akita, H.; Yamada, H.; Matsukura, H.; Nakata, T.; Oishi, T. Tetrahedron Lett. 1988, 29, 6449-6452
34. Batchelor, M. J.; Gilliespie, R. J.; Golec, J. M.; Hedgecock, C. J. R.; Jones, S. D.; Murdoch, R. Tetrahedron 1994, 50, 809-826
35. Griffith, W. P.; Ley, S. V.; Whitcomb, G. P.; White, A. D. J. Chem. Soc., Chem. Commun. 1987, 1625-1627
36. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639-666
37. Felpin, F.-X.; Lebreton, J. Eur. J. Org. Chem. 2003, 3693-3712
38. Pandit, U. K.; Overkleeft, H. S.; Borer, B. C.; Bieräugel, H. Eur. J. Org. Chem. 1999, 959-968
39. Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238
40. For RCM closure to a nine-membered ether ring: Crimmins, M. T.; Brown, B. H. J. Am. Chem. Soc. 2004, 126, 10264-10266
41. Our survey of the literature indicates fewer than 20 examples of related hexahydro azocines. See: Tymoshenko, D. O. Nine Membered Rings. In Comprehensive Heterocyclic Chemistry (CHEC) III; Katrizky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K., Eds.; Elsevier Science Ltd.: New York, 2008; pp 1-50.
42. For a leading reference, see: Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452.
43. Dess, D. B.; Martin, J. C. J. Org. Chem. 1999, 64, 7202-7207
44. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287
45. Nicolaou, K. C.; Li, A.; Edmonds, D. J. Angew. Chem., Int. Ed. 2006, 45, 7086-7090
46. Nguyen, T. M.; Siefert, R. J.; Mowrey, D. R.; Lee, D. Org. Lett. 2002, 4, 3959-3962