Domino metathesis reactions for the synthesis of fused tricyclic frameworks

Synlett

Volumn , Issue 2, 2005, Pages 235-238

  Funel, Jacques Alexis ^a   Prunet, Joëlle ^a  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

Domino reactions; Fused ring systems; Metathesis; Polycycles; Ring opening metathesis

Indexed keywords

KETONE; POLYCYCLIC AROMATIC COMPOUND; TRICYCLIC AROMATIC COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DOMINO METATHESIS; REACTION ANALYSIS; RING CLOSING METATHESIS; RING OPENING; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 13844270576     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-837200     Document Type: Article

References (21)

1. For recent reviews: (a) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012.
2. (b) Grubbs, R. H.; Trnka, R. R. Acc. Chem. Res. 2001, 34, 18; and references cited therein.
3. For a review on cross-metathesis: Connon, S. T.; Blechert, S. Angew. Chem. Int. Ed. 2003, 42, 1900.
4. Tietze, L. F. Chem. Rev. 1996, 96, 115.
5. Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634.
6. Stragies, R.; Blechert, S. Synlett 1998, 169.
7. Schrock, R. R.; Hoveyda, A. H. Angew. Chem. Int. Ed. 2003, 42, 4592; and references cited therein.
8. For a recent account see: Arjona, A.; Csákÿ, A. G.; Murcia, M. C.; Plumet, J. Eur. J. Org. Chem. 2003, 611.
9. Hagiwara, H.; Katsumi, T.; Endou, S.; Hoshi, T.; Suzuki, T. Tetrahedron 2002, 58, 6651.
10. Wrobleski, A.; Sahasrabudhe, K.; Aubé, J. J. Am. Chem. Soc. 2004, 126, 5475.
11. Rosenblum, M. J. Am. Chem. Soc. 1957, 79, 3179.
12. Lipshutz, B. H.; Ellsworth, E. L.; Dimock, S. H.; Smith, R. A. J. J. Am. Chem. Soc. 1990, 112, 4404.
13. Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100.
14. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
15. Under these conditions, compound 2 did not lead to any tricyclic adduct.
16. +: 189.1279. Found: 189.1275.
17. 26OSi: C, 74.39; H, 9.55. Found: C, 74.59; H, 9.39.
18. See ref.5 and ref.7
19. For detailed studies of this aspect in the opening of related norbornene systems see: (a) Ref.7
20. (b) Mayo, P.; Tam, W. Tetrahedron 2002, 55, 9513.
21. Weeresakare, G. M.; Liu, Z.; Rainier, J. D. Org. Lett. 2004, 6, 1625.