A protecting group free synthesis of (±)-neostenine via the [5 + 2] photocycloaddition of maleimides

Journal of Organic Chemistry

Volumn 73, Issue 17, 2008, Pages 6497-6505

  Lainchbury, Michael D ^a   Medley, Marcus I ^a   Taylor, Piers M ^a   Hirst, Paul ^a   Dohle, Wolfgang ^a   Booker Milburn, Kevin I ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS;

CHEMICAL EQUATIONS; MALEIMIDES; PHOTO CYCLOADDITION; SYNTHESIS OF;

SYNTHESIS (CHEMICAL);

3,4 DICHLORO 1 [2 97 ETHYL 2 OXO 2,3,3A,4,7,7A HEXAHYDROBENZOFURAN 4 YL)ETHYL] 1H PYRROLE 2,5 DIONE; ALKALOID; AZEPINE DERIVATIVE; COPPER DERIVATIVE; CYCLOHEXANE; FURAN; LACTONE; MALEIMIDE DERIVATIVE; NEOSTENINE; PYRROLO[1,2 A]AZEPINE; UNCLASSIFIED DRUG;

ARTICLE; BATCH REACTOR; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; DRUG SYNTHESIS; PHOTOCYCLOADDITION; REACTOR; STEMONACEAE;

ALKALOIDS; AZEPINES; CYCLOHEXANES; FURANS; LACTONES; MALEIMIDES; MODELS, CHEMICAL; PHOTOCHEMISTRY; PYRROLES; STEMONACEAE; STEREOISOMERISM;

EID: 51549106272     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801108h     Document Type: Article

References (51)

1. Pilli, R. A.; Ferreira de Oliveira, M. d. C. Nat. Prod. Rep 2000, 17, 117.
2. (a) Chung, H.-S.; Hon, P.-M.; Lin, G.; But, P. P-H.; Dong, H. Planta Med. 2003, 69, 914.
3. (b) Leung, P. H. H.; Zhang, L.; Zuo, Z.; Lin, G. Planta Med. 2006, 72, 211.
4. Götz, M.; Strunz, G. M. Tuberostemonine and Related Compounds: The Chemistry of Stemona Alkaloids. In Alkaloids, vol. 9, ed. Wiesner, G. Ed.; MTP, International Review of Sciences: Organic Chemistry, Series One; Butterworths: London, 1973; pp 143-160.
5. Shinozaki, H.; Ishida, M. Brain Res. 1985, 334, 33.
6. (a) Cheng, C. Y.; Hart, D. J. Org. Chem. 1990, 55, 6236.
7. (b) Cheng, C. Y.; Hart, D. J. Org. Chem. 1993, 58, 3840.
8. (a) Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773.
9. (b) Morimoto, Y.; Iwahashi, M. Synlett 1995, 1221.
10. (c) Morimoto, Y.; Iwahashi, M.; Nishida, K.; Hayashi, Y.; Shirahama, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 904.
11. (d) Morimoto, Y.; Iwahashi, M.; Kinoshita, T.; Nishida, K. Chem. Eur. J. 2001, 7, 4107.
12. (a) Ginn, J. D.; Padwa, A. Org. Lett. 2002, 4, 1515.
13. (b) Padwa, A.; Ginn, J. D. J. Org. Chem. 2005, 70, 5197.
14. (a) Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1995, 117, 11106.
15. (b) Goldstein, D. M.; Wipf, P. Tetrahedron Lett. 1996, 37, 739.
16. (a) Wipf, P.; Spencer, S. R.; Takahashi, H. J. Am. Chem. Soc. 2002, 124, 14848.
17. (b) Wipf, P.; Spencer, S. R. J. Am. Chem. Soc. 2005, 127, 225.
18. (a) Aubé, J.; Milligan, G. L. J. Am. Chem. Soc. 1991, 113, 8965.
19. (b) Aubé, J.; Milligan, G. L.; Mossman, C. J. J. Org. Chem. 1992, 57, 1635.
20. (c) Milligan, G. L.; Mossman, C. J.; Aube, J. J. Am. Chem. Soc. 1995, 117, 10449.
21. (d) Desai, P.; Schildknegt, K.; Agrios, K. A.; Mossman, C.; Milligan, G. L.; Aubé, J. J. Am. Chem. Soc. 2000, 122, 7226.
22. (e) Zeng, Y.; Reddy, S.; Hirt, E.; Aubé, J. Org. Lett. 2004, 6, 4993.
23. (f) Zeng, Y.; Aubé, J. J. Am. Chem. Soc. 2005, 127, 15712.
24. Frankowski, K. J.; Golden, J. E.; Zeng, Y.; Lei, Y.; Aubé, J. J. Am. Chem. Soc. 2008, 130, 6018.
25. Booker-Milburn, K. I.; Hirst, P.; Charmant, J. P. H.; Taylor, L. H. J. Angew. Chem., Int. Ed. 2003, 42, 1642.
26. (a) Booker-Milburn, K. I.; Cowell, J. K. Tetrahedron Lett. 1996, 37, 2177.
27. (b) Booker-Milburn, K. I.; Cowell, J. K.; Delgado Jiménez, F.; Sharpe, A.; White, A. J. Tetrahedron 1999, 55, 5875.
28. (c) Booker-Milburn, K. I.; Delgado Jiménez, F.; Sharpe, A. Tetrahedron 1999, 55, 5889.
29. (a) Booker-Milburn, K. I.; Costin, N. J.; Dainty, R. F.; Patel, D.; Sharpe, A. Tetrahedron Lett. 1998, 39, 7423.
30. (b) Booker-Milburn, K. I.; Anson, C. E.; Clissold, C.; Costin, N. J.; Dainty, R. F.; Murray, M.; Patel, D.; Sharpe, A. Eur. J. Org. Chem. 2001, 1473.
31. For related phthalimide photochemistry, see: (a) Mazzocchi, P. H.; Bowen, M. J.; Narain, N. K. J. Am. Chem. Soc. 1977, 99, 7063.
32. (b) Mazzocchi, P. H.; Minamikawa, S.; Bowen, M. J. J. Org. Chem. 1978, 43, 3079.
33. (c) Mazzocchi, P. H.; Minamikawa, S.; Wilson, P. J. Org. Chem. 1979, 44, 1186.
34. (d) Mazzocchi, P. H.; Wilson, P.; Khachik, F.; Klingler, L.; Minamikawa, S. J. Org. Chem. 1983, 48, 2981.
35. Davies, D. M. E.; Murray, C.; Berry, M.; Orr-Ewing, A. J.; Booker-Milburn, K. I. J. Org. Chem. 2007, 72, 1449.
36. Dudin, L. F.; Booker-Milburn, K. I.; Anson, C. E.; Guile, S. D. Org. Lett. 2001, 3, 3005.
37. Protecting group free approaches to 7-desmethylasteriscanolide: (a) Booker-Milburn, K. I.; Cowell, J. K.; Harris, L. J. Tetrahedron 1997, 53, 12319.
38. Pogostol and kessane: (b) Booker-Milburn, K. I.; Jenkins, H.; Mohr, P. Org. Lett. 2003, 5, 3309.
39. For a recent example of the benefits of protecting group free strategies in complex alkaloid synthesis, see: Baran, P. S.; Maimone, T. J.; Richter, J. M. Nature 2007, 446, 404.
40. Paquette, L. A.; Kravetz, T. M.; Charumilind, P. Tetrahedron 1986, 42, 1779.
41. Grieco, P. A.; Srinivasan, C. V. J. Org. Chem. 1981, 46, 2591.
42. Curran, D. P.; Chen, M. H.; Leszcweski, D.; Elliot, R. L.; Rakiewiecz, D. M. J. Org. Chem. 1986, 51, 1612.
43. Bergner, E. J.; Helmchen, G. Eur. J. Org. Chem. 2000, 6, 419.
44. N'Zoutani, M. A.; Pancrazi, A.; Ardisson, J. Synlett 2001, 769.
45. Hook, B. D. A.; Dohle, W.; Hirst, P. R.: Pickworth, M.; Berry, M. B.; Booker-Milburn, K. I. J. Org. Chem. 2005, 70, 7558.
46. (a) Danishefsky, S.; Kitahara, T.; Schuda, P. F.; Etheredge, S. J. J. Am. Chem. Soc. 1976, 98, 3028.
47. (b) Danishefsky, S.; Schuda, P. F.; Kitahara, T.; Etheredge, S. J. J. Am. Chem. Soc. 1977, 99, 6066.
48. Yasuda, M.; Onishi, Y.; Ueba, M.; Miyai, T.; Baba, A. J. Org. Chem. 2001, 66, 7741.
49. Barton, D. H. R.; Jaszberenyi, J. Cs. Tetrahedron. Lett. 1989, 30, 2619.
50. Yanagisawa, A.; Watanabe, T.; Kikuchi, T.; Yamamoto, H. J. Org. Chem. 2000, 65, 2979.
51. Kuwano, R.; Takahashi, M.; Ito, Y. Tetrahedron. Lett. 1998, 39, 1017.