β-silyl styrene as a dienophile in the cycloaddition with 3,5-dibromo-2-pyrone for the total synthesis of (±)-pancratistatin

Organic Letters

Volumn 13, Issue 21, 2011, Pages 5890-5892

  Jung, Yong Geun ^a   Kang, Ho Ung ^a   Cho, Hyun Kyu ^a   Cho, Cheon Gyu ^a  

^a Hanyang University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

3,5 DIBROMO 2 PYRONE; 3,5-DIBROMO-2-PYRONE; AMARYLLIDACEAE ALKALOID; ISOQUINOLINE DERIVATIVE; PANCRATISTATIN; PYRONE DERIVATIVE; SILICON; STYRENE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

AMARYLLIDACEAE ALKALOIDS; CYCLIZATION; ISOQUINOLINES; MOLECULAR STRUCTURE; PYRONES; SILICON; STYRENE;

EID: 80055084410     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202525a     Document Type: Article

References (39)

1. Pettit, G. R.; Gaddamidi, V.; Cragg, G. M.; Herald, D. L.; Sagawa, Y. J. Chem. Soc., Chem. Commun. 1984, 1693
2. Manpadi, M.; Kornienko, A. Org. Prep. Proced. Int. 2008, 40, 107
3. Chapleur, Y.; Chretien, F.; Ahmed, S. I.; Khaldi, M. Curr. Org. Synth. 2006, 3, 341
4. Jin, Z. Nat. Prod. Rep. 2005, 22, 111
5. Rinner, U.; Hudlicky, T. Synlett 2005, 365
6. Prabhakar, S.; Tavares, M. R. Alkaloids Chem. Biol. 2001, 15, 433
7. Polt, R. Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI: Greenwich, CT, 1997; Vol. 3, p 109.
8. Martin, S. F. In The Alkaloid; Bross, A. R., Ed.; Academic: New York, 1987; Vol. 40, p 251. For reviews or leading articles on the biological activities, see
9. Pettit, G. R.; Orr, B.; Ducki, S. Anti-Cancer Drug Des. 2000, 15, 389
10. Gabrielsen, B.; Monath, T. P.; Huggins, J. W.; Kirsi, J. J.; Hollingshead, M.; Shannon, W. M.; Pettit, G. R. In Natural Products as Antiviral Agents; Chu, C. K.; Cutler, H. G., Eds.; Plenum: New York, 1992; pp 121-135.
11. Pettit, G. R.; Gaddamidi, V.; Cragg, G. M.; Herald, D. L.; Singh, S. B.; Cragg, G. M.; Schmidt, J. M.; Boettner, F. E.; Williams, M.; Sagawa, Y. J. Nat. Prod. 1986, 49, 995
12. Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829
13. Tian, X.; Hudlicky, T.; Konigsberger, K. J. Am. Chem. Soc. 1995, 117, 3643
14. Trost, B. M.; Pulley, S. R. J. Am. Chem. Soc. 1995, 117, 10143
15. Doyle, T. J.; Hendrix, M.; Van Derveer, D.; Javanmard, S; Haseltine, J. Tetrahedron 1997, 53, 11153
16. Magnus, P.; Sebhat, I. K. J. Am. Chem. Soc. 1998, 120, 5341
17. Rigby, J. H.; Maharoof, U. S. M.; Mateo, M. E. J. Am. Chem. Soc. 2000, 122, 6624
18. Pettit, G. R.; Melody, N.; Herald, D. L. J. Org. Chem. 2001, 66, 2583
19. Kim, S.; Ko, H.; Kim, E.; Kim, D. Org. Lett. 2002, 4, 1343
20. Li, M.; Wu, A.; Zhou, P. Tetrahedron Lett. 2006, 47, 3707
21. Chang, J. H.; Kang, H.-U.; Jung, I.-H.; Cho, C.-G. Org. Lett. 2010, 12, 2016
22. Tam, N. T.; Jung, E.-J.; Cho, C.-G. Org. Lett. 2010, 12, 2012
23. Tam, N. T.; Cho, C.-G. Org. Lett. 2008, 10, 601
24. Tam, N. T.; Chang, J.; Jung, E.-J.; Cho, C.-G. J. Org. Chem. 2008, 73, 6258
25. Shin, I.-J.; Choi, E.-S.; Cho, C.-G. Angew. Chem., Int. Ed. 2007, 46, 2303
26. Tam, N. T.; Cho, C.-G. Org. Lett. 2007, 9, 3319
27. Kim, H.-Y.; Cho, C.-G. Prog. Heterocycl. Chem. 2007, 18, 1
28. Ryu, K.; Cho, Y.-S.; Cho, C.-G. Org. Lett. 2006, 8, 3343
29. Sheshenev, A.; Baird, M. S.; Bolesov, I. G.; Shshkov, A. S. Tetrahedron 2009, 65, 10552
30. Eisch, J. J.; Foxton, M. W. J. Org. Chem. 1971, 36, 3520
31. Slaugh, L. H. Tetrahedron 1966, 22, 1741
32. Cho, C.-G.; Kim, Y.-W.; Lim, Y.-K.; Park, J.-S.; Lee, H.; Koo, S. J. Org. Chem. 2002, 67, 290
33. Molander, G. A.; Felix, L. A. J. Org. Chem. 2005, 70, 3956
34. Zhang, H.; Padwa, A. Org. Lett. 2006, 8, 247
35. Ko, H.; Kim, E.; Park, J. E.; Kim, D.; Kim, S. J. Org. Chem. 2004, 69, 112
36. Rigby, J. H.; Maharoof, U. S. M.; Mateo, M. E. J. Am. Chem. Soc. 2000, 122, 6624
37. Hudlicky, T.; Rinner, U.; Gonzalez, D.; Akgun, H.; Schilling, S.; Siengalewicz, P.; Martinot, T.; Pettit, G. R. J. Org. Chem. 2002, 67, 8726
38. Cavdar, H.; Saracoglu, N. Tetrahedron 2009, 65, 985
39. Banwell, M. G.; Bisset, B. D.; Busato, S.; Cowden, C. J.; Hockless, D. C. R.; Holman, J. W.; Read, R. W.; Wu, A. W. J. Chem. Soc., Chem. Commun. 1995, 2551