Synthesis of the core ring system of the yuzurimine-type daphniphyllum alkaloids by cascade condensation, cyclization, cycloaddition chemistry

Journal of Organic Chemistry

Volumn 76, Issue 7, 2011, Pages 2360-2366

  Coldham, Iain ^a   Watson, Luke ^a   Adams, Harry ^a   Martin, Nathaniel G ^b  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ALCOHOLS; CYCLOADDITION CHEMISTRY; INTRAMOLECULAR DIPOLAR CYCLOADDITION; ISOXAZOLIDINES; NATURAL PRODUCTS; NITRONES; RING OPENING; RING SYSTEMS; TANDEM CYCLIZATION;

ALCOHOLS; AMINES; CYCLOADDITION; METABOLITES;

CYCLIZATION;

1,3 OXAZINE DERIVATIVE; ALKALOID; AMINOALCOHOL; DAPHCALYCIC ACID; DAPHCALYCINE; HYDROXYLAMINE; ISOXAZOLIDINE DERIVATIVE; NITRONE; UNCLASSIFIED DRUG; YUZURIMINE;

ARTICLE; CYCLIZATION; CYCLOADDITION; DAPHNIPHYLLUM; NONHUMAN; RING OPENING; SHRUB; SYNTHESIS;

ALDEHYDES; ALKALOIDS; AMINO ALCOHOLS; CYCLIZATION; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; MOLECULAR STRUCTURE; OXAZINES; STEREOISOMERISM;

EID: 79953187932     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2000868     Document Type: Article

References (41)

1. Kobayashi, J.; Kubota, T. Nat. Prod. Rep. 2009, 26, 936
2. Dong, M.; Zhang, M. L.; Shi, Q. W.; Gu, Y. C.; Kiyota, H. Curr. Org. Chem. 2009, 13, 646
3. Kobayashi, J.; Morita, H. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 2003; Vol. 60, pp 165 - 205.
4. Heathcock, C. H.; Hansen, M. M.; Ruggeri, R. B.; Kath, J. C. J. Org. Chem. 1992, 57, 2544
5. Heathcock, C. H.; Stafford, J. A. J. Org. Chem. 1992, 57, 2566
6. Heathcock, C. H.; Stafford, J. A.; Clark, D. L. J. Org. Chem. 1992, 57, 2575
7. Heathcock, C. H.; Ruggeri, R. B.; McClure, K. F. J. Org. Chem. 1992, 57, 2585
8. Heathcock, C. H.; Kath, J. C.; Ruggeri, R. B. J. Org. Chem. 1995, 60, 1120
9. Denmark, S. E.; Baiazitov, R. Y.; Nguyen, S. T. Tetrahedron 2009, 65, 6535
10. Denmark, S. E.; Nguyen, S. T.; Baiazitov, R. Y. Heterocycles 2008, 76, 143
11. Denmark, S. E.; Baiazitov, R. Y. J. Org. Chem. 2006, 71, 593
12. Ueda, M.; Walczak, M. A. A.; Wipf, P. Tetrahedron Lett. 2008, 49, 5986
13. Solé, D.; Urbaneja, X.; Bonjoch, J. Org. Lett. 2005, 7, 5461
14. Cordero-Vargas, A.; Urbaneja, X.; Bonjoch, J. Synlett 2007, 2379
15. Ikeda, S.; Shibuya, M.; Kanoh, N.; Iwabuchi, Y. Org. Lett. 2009, 11, 1833
16. Tanabe, K.; Fujie, A.; Ohmori, N.; Hiraga, Y.; Kojima, S.; Ohkata, K. Bull. Chem. Soc. Jpn. 2007, 80, 1597
17. Coldham, I.; Burrell, A. J. M.; White, L. E.; Adams, H.; Oram, N. Angew. Chem., Int. Ed. 2007, 46, 6159
18. Burrell, A. J. M.; Coldham, I.; Watson, L.; Oram, N.; Pilgram, C. D.; Martin, N. G. J. Org. Chem. 2009, 74, 2290
19. Burrell, A. J. M.; Coldham, I.; Oram, N. Org. Lett. 2009, 11, 1515
20. Burrell, A. J. M.; Watson, L.; Martin, N. G.; Oram, N.; Coldham, I. Org. Biomol. Chem. 2010, 8, 4530
21. Coldham, I.; Jana, S.; Watson, L.; Pilgram, C. D. Tetrahedron Lett. 2008, 49, 5408
22. Coldham, I.; Jana, S.; Watson, L.; Martin, N. G. Org. Biomol. Chem. 2009, 7, 1674
23. Coldham, I.; Burrell, A. J. M.; Guerrand, H. D. S.; Oram, N. Org. Lett. 2011, 13, 1267
24. Bitar, H. E.; Nguyen, V. H.; Gramain, A.; Sevenet, T.; Bodo, B. Tetrahedron Lett. 2004, 45, 515
25. Jossang, A.; Bitar, H. E.; Pham, V. C.; Sevenet, T. J. Org. Chem. 2003, 68, 300
26. Mu, S.-Z.; Wang, Y.; He, H.-P.; Yang, X.-W.; Wang, Y.-H.; Di, Y.-T.; Lu, Y.; Chang, Y.; Hao, X.-J. J. Nat. Prod. 2006, 69, 1065
27. Li, C.-S.; Di, Y.-T.; Mu, S.-Z.; He, H.-P.; Zhang, Q.; Fang, X.; Zhang, Y.; Li, S.-L.; Lu, Y.; Gong, Y.-Q.; Hao, X.-J. J. Nat. Prod. 2008, 71, 1202
28. For some examples of N-alkylation of an oxime then nitrone cycloaddition, see: Brasholz, M.; Macdonald, J. M.; Saubern, S.; Ryan, J. H.; Holmes, A. B. Chem.-Eur. J. 2010, 16, 11471
29. Brasholz, M.; Johnson, B. A.; Macdonald, J. M.; Polyzos, A.; Tsanaktsidis, J.; Saubern, S.; Holmes, A. B.; Ryan, J. H. Tetrahedron 2010, 66, 6445
30. Flick, A. C.; Caballero, M. J. A.; Padwa, A. Tetrahedron 2010, 66, 3643
31. Flick, A. C.; Caballero, M. J. A.; Lee, H. I.; Padwa, A. J. Org. Chem. 2010, 75, 1992
32. Stearman, C. J.; Wilson, M.; Padwa, A. J. Org. Chem. 2009, 74, 3491
33. Karatholuvhu, M. S.; Sinclair, A.; Newton, A. F.; Alcaraz, M.-L.; Stockman, R. A.; Fuchs, P. L. J. Am. Chem. Soc. 2006, 128, 12656
34. For a review, see: Burrell, A. J. M.; Coldham, I. Curr. Org. Synth. 2010, 7, 312
35. Ellames, G. J.; Hewkin, C. T.; Jackson, R. F. W.; Smith, D. I.; Standen, S. P. Tetrahedron Lett. 1989, 30, 3471
36. Kraft, P.; Popaj, K. Eur. J. Org. Chem. 2004, 4995
37. Tormo, J.; Verdaguer, X.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron 1996, 52, 14021
38. Dandapani, S.; Jeske, M.; Curran, D. P. J. Org. Chem. 2005, 70, 9447
39. Mycka, R. J.; Steward, O. W.; Fleming, F. F. Org. Lett. 2010, 12, 3030
40. Harrison, C. R.; Hodge, P.; Hunt, B. J.; Khoshdel, E.; Richardson, G. J. Org. Chem. 1983, 48, 3721
41. Xie, Z.-F.; Suemune, H.; Sakai, K. Tetrahedron: Asymmetry 1993, 4, 973