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Intramolecular Allylation to Coerulescine and a New Route to Formal Synthesis of Horsfiline

  • Kim, Min-Hye (Department of Chemistry, College of Natural Science, Chungnam National University) ;
  • Kim, Gun-Cheol (Department of Chemistry, College of Natural Science, Chungnam National University)
  • Received : 2012.02.07
  • Accepted : 2012.03.03
  • Published : 2012.06.20

Abstract

Keywords

References

  1. Usui, T.; Kondoh, M.; Cui, C. B.; Mayumi, T.; Osada, H. Biochem. J. 1998, 333, 543.
  2. Fensome, A.; Adams, W. R.; Adams, A. L.; Berrodin, T. J.; Cohen, J.; Huselton, C.; Illenberger, A.; Kern, J. C.; Hudak, V. A.; Marella, M. A.; Melenski, E. G.; McComas, C. C.; Mugford, C. A.; Slayden, O. D.; Yudt, M.; Zhang, Z. M.; Zhang, P. W.; Zhu, Y.; Winneker, R. C.; Wrobel, J. E. J. Med. Chem. 2008, 51, 1861. https://doi.org/10.1021/jm701080t
  3. Stump, C. A.; Bell, I. M.; Bednar, R. A.; Bruno, J. G.; Fay, J. F.; Gallicchio, S. N.; Johnston, V. K.; Moore, E. L.; Mosser, S. D.; Quigley, A. G.; Salvatore, C. A.; Theberge, C. R.; Zartman, C. B.; Zhang, X. F.; Kane, S. A.; Graham, S. L.; Vacca, J. P.; Williams, T. M. Bioorg. Med. Chem. Lett. 2009, 19, 214. https://doi.org/10.1016/j.bmcl.2008.10.106
  4. Deppermann, N.; Thomanek, H.; Prenzel, A. H. G. P.; Maison, W. J. Org. Chem. 2010, 75, 5994. https://doi.org/10.1021/jo101401z
  5. White, J. D.; Li, Y.; Ihle, D. C. J. Org. Chem. 2010, 75, 3569. https://doi.org/10.1021/jo1002714
  6. Jiang, K.; Jia, Z.-J.; Yin, X.; Wu, L.; Chen, Y.-C. Org. Lett. 2010, 12, 2766. https://doi.org/10.1021/ol100857s
  7. Hari, G. S.; Lee, Y. R. Synthesis 2010, 453.
  8. Liang, B.; Kalidindi, S.; Porco, J. A.; Stephenson, C. R. J. Org. Lett. 2010, 12, 572. https://doi.org/10.1021/ol902764k
  9. Chen, X. H.; Wei, Q.; Luo, S. W.; Xiao, H.; Gong, L. Z. J. Am. Chem. Soc. 2009, 131, 13819. https://doi.org/10.1021/ja905302f
  10. Ruck, R. T.; Huffman, M. A.; Kim, M. M.; Shevlin, M.; Kandur, W. V.; Davies, I. W. Angew. Chem., Int. Ed. 2008, 47, 4711. https://doi.org/10.1002/anie.200800549
  11. Chen, X. H.; Wei, Q.; Luo, S. W.; Xiao, H.; Gong, L. Z. J. Am. Chem. Soc. 2009, 131, 13819. https://doi.org/10.1021/ja905302f
  12. Ruck, R. T.; Huffman, M. A.; Kim, M. M.; Shevlin, M.; Kandur, W. V.; Davies, I. W. Angew. Chem., Int. Ed. 2008, 47, 4711. https://doi.org/10.1002/anie.200800549
  13. Marsden, S. P.; Watson, E. L.; Raw, S. A. Org. Lett. 2008, 10, 2905. https://doi.org/10.1021/ol801028e
  14. Trost, B. M.; Brennan, M. K. Org. Lett. 2006, 8, 2027. https://doi.org/10.1021/ol060298j
  15. Murphy, J. A.; Tripoli, R.; Khan, T. A.; Mali, U. W. Org. Lett. 2005, 7, 3287. https://doi.org/10.1021/ol051095i
  16. Onishi, T.; Sebahar, P. R.; Williams, R. M. Tetrahedron 2004, 60, 9503. https://doi.org/10.1016/j.tet.2004.07.047
  17. Lo, M. M. C.; Neumann, C. S.; Nagayama, S.; Perlstein, E. O.; Schreiber, S. L. J. Am. Chem. Soc. 2004, 126, 16077. https://doi.org/10.1021/ja045089d
  18. Wang, H.; Ganesan, A. J. Org. Chem. 2000, 65, 4685. https://doi.org/10.1021/jo000306o
  19. Anderton, N.; Cockrum, P. A.; Colegate, S. M.; Edgar, J. A.; Flower, K.; Vit, I.; Willing, R. I. Phytochemistry 1998, 45, 437.
  20. Anderton, N.; Cockrum, P. A.; Colegate, S. M.; Edgar, J. A.; Flower, K.; Gardner, D.; Willing, R. I. Phytochemistry 1999, 51, 153 https://doi.org/10.1016/S0031-9422(98)00725-0
  21. Jossang, A.; Jossang, P.; Hadi, H. A.; Sevenet, T.; Bodo, B. J. Org. Chem. 1991, 56, 6527. https://doi.org/10.1021/jo00023a016
  22. Kim, G.; Kim, J. H.; Lee, K. Y. J. Org. Chem. 1991, 56, 6527. https://doi.org/10.1021/jo00023a016
  23. Tuan, L. A.; Kim, G. Tetrahedron Lett. 2010, 51, 2354. https://doi.org/10.1016/j.tetlet.2010.02.136
  24. Tuan, L. A.; Kim, G. Bull. Korean. Chem. Soc. 2010, 31, 1800. https://doi.org/10.5012/bkcs.2010.31.6.1800
  25. Franckerviius, V.; Cuthbertson, J. D.; Pickworth, M.; Pugh, D. S.; Taylor, J. K. Org. Lett. 2011, 13, 4264. https://doi.org/10.1021/ol201613a
  26. Keith, J. A.; Behenna, D. C.; Mohr, J. T.; Ma, S.; Marinescu, S. C.; Oxgaard, J.; Stoltz, B. M.; Goddard, W. A., III. J. Am. Chem. Soc. 2007, 129, 16077.
  27. Trost, B. M.; Stiles, D. T. Org. Lett. 2007, 9, 2763. https://doi.org/10.1021/ol070971k
  28. Weaver, J. D.; Recio, A.; Grenning, A. J.; Tunge, J. A. Chem. Rev. 2011, 111, 1846. https://doi.org/10.1021/cr1002744
  29. Mohr, J. T.; Stoltz, B. M. Chem.-Asian J. 2007, 2, 1476. https://doi.org/10.1002/asia.200700183

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