Formal and total synthesis of (±)-cycloclavine

Tetrahedron Letters

Volumn 55, Issue 1, 2014, Pages 197-199

  Jabre, Nitinkumar D ^a   Watanabe, Teruki ^a   Brewer, Matthias ^a  

^a UNIVERSITY OF VERMONT   (United States)

Author keywords

1,3 Dipolar cycloaddition; Cycloclavine; Ergot alkaloid; Natural product synthesis; Ring fragmentation

Indexed keywords

AZOMETHINE YLIDE; CYCLOCLAVINE; CYCLOPROPANE; INDOLE ALKALOID; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; CYCLOPROPANATION; DIPOLE; DRUG STRUCTURE; DRUG SYNTHESIS; FRAGMENTATION REACTION; PRECURSOR; RING FRAGMENTATION REACTION;

EID: 84890157721     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.10.152     Document Type: Article

References (31)

1. D. Stauffacher, P. Niklaus, H. Tscherter, H.P. Weber, and A. Hofmann Tetrahedron 25 1969 5879 5887
2. M. Incze, G. Doernyei, I. Moldvai, E. Temesvari-Major, O. Egyed, and C. Szántay Tetrahedron 64 2008 2924 2929
3. F.R. Petronijevic, and P. Wipf J. Am. Chem. Soc. 133 2011 7704 7707
4. K. Teranishi, S. Hayashi, S.I. Nakatsuka, and T. Goto Tetrahedron Lett. 35 1994 8173 8176
5. K. Teranishi, S. Hayashi, S. Nakatsuka, and T. Goto Synthesis 7 1995 506 508
6. C. Draghici, Q. Huang, and M. Brewer J. Org. Chem. 74 2009 8410 8413
7. Z. Zhang, G.M. Giampa, C. Draghici, Q.F. Huang, and M. Brewer Org. Lett. 15 2013 2100 2103
8. A. Bayir, C. Draghici, and M. Brewer J. Org. Chem. 75 2010 296 302
9. C. Draghici, and M. Brewer J. Am. Chem. Soc. 130 2008 3766 3767
10. G.M. Rubottom, M.A. Vazquez, and D.R. Pelegrina Tetrahedron Lett. 15 1974 4319 4322
11. Y.Y. Novikov, and P. Sampson Org Lett 5 2003 2263 2266
12. M. Ruiz, J.D. Sanchez, P. Lopez-Alvarado, and J.C. Menendez Tetrahedron 68 2012 705 710
13. D.F. Taber, and P. Guo J. Org. Chem. 73 2008 9479 9481
14. Z. Wang Kishner Decomposition 2010 John Wiley & Sons, Inc. In Comprehensive Organic Name Reactions and Reagents
15. M.A. Chowdhury, H. Senboku, and M. Tokuda Tetrahedron Lett. 44 2003 3329 3332
16. E.J. Corey, and M. Chaykovsky J. Am. Chem. Soc. 87 1965 1353 1364
17. K. Wang, and Z. Liu Synth. Commun. 40 2010 144 150
18. Inoue, T.; Watanabe, S.; Yamagishi, T.; Arano, Y.; Morita, M.; Shimada, K. Aryl substituted carboxamide derivatives as calcium or sodium channel blockers. WO2010137351, 2010.
19. D. Yohannes, K. Procko, L.A. Lebel, C.B. Fox, and B.T. O'Neill Bioorg. Med. Chem. Lett. 18 2008 2316 2319
20. H. Lebel, J.-F. Marcoux, C. Molinaro, and A.B. Charette Chem. Rev. 103 2003 977 1050
21. K. Fujii, K. Shiine, T. Misaki, and T. Sugimura Appl. Organomet. Chem. 27 2013 69 72
22. A.B. Charette, and M.-C. Lacasse Org. Lett. 4 2002 3351 3353
23. A.B. Charette, and H. Lebel J. Org. Chem. 60 1995 2966 2967
24. A. Voituriez, L.E. Zimmer, and A.B. Charette J. Org. Chem. 75 2010 1244 1250
25. J.C. Lorenz, J. Long, Z. Yang, S. Xue, Y. Xie, and Y. Shi J. Org. Chem. 69 2004 327 334
26. A.B. Charette, H. Juteau, H. Lebel, and C. Molinaro J. Am. Chem. Soc. 120 1998 11943 11952
27. G.A. Molander, and L.S. Harring J. Org. Chem. 54 1989 3525 3532
28. Simoneau, B.; Thavonekham, B.; Landry, S.; O'meara, J.; Yoakim, C.; Faucher, A.-M. Non-nucleoside reverse transcriptase inhibitors WO2004050643, 2004.
29. G. Brunner, L. Eberhard, J. Oetiker, and F. Schroder J. Org. Chem. 73 2008 7543 7554
30. J.M. Concellón, H. Rodríguez-Solla, C. Méjica, and E.G. Blanco Org. Lett. 9 2007 2981 2984
31. J.-F. Fournier, S. Mathieu, and A.B. Charette J. Am. Chem. Soc. 127 2005 13140 13141