A Concise, metathesis based approach to construction of the lepadiformine/cylindricine tricyclic framework

Tetrahedron

Volumn 66, Issue 32, 2010, Pages 5955-5961

  Zou, Jiwen ^a   Cho, Dae Won ^a   Mariano, Patrick S ^a  

^a UNIVERSITY OF NEW MEXICO   (United States)

Author keywords

Metathesis; Pyridinium salt photochemistry; Ruthenium carbene catalysis

Indexed keywords

2 PENTENYL 2 ETHYNYLPYROLLIDINE ACRYLAMIDE; ACRYLAMIDE DERIVATIVE; ALKALOID DERIVATIVE; CARBENE; CYLINDRICINE; LEPADIFORMINE; PROLINE; RUTHENIUM CARBENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 77955426366     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.06.027     Document Type: Article

References (35)

1. J.-F. Biard, S. Guyot, C. Roussakis, J.F. Verbist, T. Vercauteren, J.F. Weber, and K. Boukef Tetrahedron Lett. 35 1994 2691
2. M. Juge, N. Grimaud, J.-F. Biard, M.-P. Sauviat, M. Nabil, J.-F. Verbist, and J.-Y. Petit Toxicon 39 2001 1231
3. M.-P. Sauviat, J. Vercauteren, N. Grimaud, M. Juge, M. Nabil, J.-Y. Petit, and J.-F. Biard J. Nat. Prod. 69 2006 558
4. A.J. Blackman, C. Li, D.C.R. Hockless, B.W. Skelton, and A.H. White Tetrahedron 49 1993 8645
5. H. Abe, S. Aoyagi, and C. Kibayashi J. Am. Chem. Soc. 122 2000 4583
6. P. Sun, C. Sun, and S.M. Weinreb Org. Lett. 3 2001 3507
7. For a comprehensive review, see S.M. Weinreb Chem. Rev. 106 2006 2531
8. R. Ling, M. Yoshida, and P.S. Mariano J. Org. Chem. 61 1996 4439
9. Z. Zhao, E. Duesler, C. Wang, H. Guo, and P.S. Mariano J. Org. Chem. 70 2005 8508
10. L. Song, E.N. Duesler, and P.S. Mariano J. Org. Chem. 69 2004 7284
11. S. Suga, M. Watanabe, and J. Yoshida J. Am. Chem. Soc. 124 2002 14824
12. A. Deiters, and S.F. Martin Chem. Rev. 104 2004 2199
13. P. Schwab, R.H. Grubbs, and J.W. Ziller J. Am. Chem. Soc. 118 1996 100
14. M.S. Sanford, M. Ulman, and R.H. Grubbs J. Am. Chem. Soc. 123 2001 749
15. For a recent review see R.H. Grubbs, Handbook of Metathesis. Application in Organic Synthesis Vol. 2 2003 Wiley-VCH Morlenbach
16. W.J. Zuercher, M. Hashimoto, and R.H. Grubbs J. Am. Chem. Soc. 118 1996 6634
17. S.T. Diver, and A.J. Giessert Chem. Rev. 104 2004 1317
18. S.V. Mayfield, and D. Lee Chem. - Eur. J. 11 2005 6118
19. M. Mori R.H. Grubbs, Hanbook of Metathesis. Applications in Organic Synthesis Vol. 2 2003 Wiley-VCH Morlenbach 176
20. T.-L. Choi, and R.H. Grubbs Chem. Commun. 2001 2648
21. T. Honda, H. Namiki, K. Kaneda, and H. Mizutani Org. Lett. 6 2004 87
22. H. Fukumoto, J. Esumi, and S. Hatakeyama Tetrahedron Lett. 44 2003 8047
23. K. Shimizu, M. Takimoto, Y. Sato, and M. Mori J. Organomet. Chem. 691 2006 5466
24. H. Fukumoto, K. Takahashi, J. Ishihara, and S. Hatakeyama Angew. Chem., Int. Ed. 45 2006 2731
25. D. Seebach, M. Boes, R. Naef, and W.B. Schweizer J. Am. Chem. Soc. 105 1983 5390
26. E.M. Khalil, W.H. Ojala, A. Pradhan, V.D. Nair, W.B. Gleason, R.K. Mishra, and R.L. Johnson J. Med. Chem. 42 1999 628
27. M.J. Genin, P.W. Baures, and R.L. Johnson Tetrahedron Lett. 35 1994 4967
28. E.M. Khalil, N.L. Subasinghe, and R.L. Johnson Tetrahedron Lett. 37 1996 3441
29. S. Muller, B. Liepold, G.J. Roth, and H.J. Bestmann Synlett 1996 521
30. A method for preparation of a suitably protected 5-hydroxyproline derivative that can be used for this purpose is reported in K.F. McClure, P. Renold, and D.S. Kemp J. Org. Chem. 60 1995 454
31. T. Tnaiguchi, O. Tamura, M. Uchiyama, O. Muraoka, and G. Tanabe Synlett 2005 1179
32. T. Taniguchi, D. Yonei, M. Sasaki, O. Tamura, and H. Ishibashi Tetrahedron 64 2008 2634
33. Z. Zhao, and P.S. Mariano Tetrahedron 62 2006 7266
34. F. Diaba, E. Ricou, D. Sole, E. Teixido, N. Valls, and J. Bonjoch Arkivoc 2007 320
35. N. Ono, T. Yamada, T. Saito, K. Tanaka, and A. Kaji Bull. Chem. Soc. Jpn. 51 1978 2401