An efficient construction of bicyclic systems containing a seven-membered ring by tandem ring-closing metathesis reactions of dienynes

Journal of Organometallic Chemistry

Volumn 691, Issue 24-25, 2006, Pages 5181-5188

  Boyer, François Didier ^a   Hanna, Issam ^b  

^a CEMAGREF   (France)

^b LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

Dienynes; Seven membered ring; Tandem ring closing metathesis

Indexed keywords

ALCOHOLS; CATALYSIS; ESTERS; OXIDATION; PARAFFINS; SYNTHESIS (CHEMICAL);

DIENYNES; RING CLOSING METATHESIS (RCM); SEVEN MEMBERED RING; TANDEM RING CLOSING METATHESIS;

OLEFINS;

EID: 33751236489     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2006.07.014     Document Type: Article

References (37)

1. For selected recent reports concerning the construction of (5-7) and (6-7) bicyclic systems using transition metal-catalyzed reactions see:. Battiste M.A., Pelphrey P.M., and Wright D. Chem. Eur. J. 12 (2006) and references cited therein
2. Trost B.M., Schen H.C., Horne D.B., Toste F.D., Steinmetz B.G., and Koradin C. Chem. Eur. J. 11 (2005) 2577-2590
3. Pfeiffer M.W.B., and Phillips A.J. J. Am. Chem. Soc. 127 (2005) 5334-5335
4. Wender P.A., Bi F.C., Brodney M.A., and Gosselin F. Org. Lett. 3 (2001) 2105-2108 and references cited therein
5. Sarpong R., Su J.T., and Stoltz B.M.J. Am. Chem. Soc. 125 (2003) 13624-13625
6. For recent reviews concerning ring-closing metathesis reactions, see:. Astruc D. New J. Chem. 29 (2005) 42-56
7. Grubbs R.H. Tetrahedron 60 (2004) 7117-7140
8. In: Grubbs R.H. (Ed). Handbook of Metathesis Vol. 2 (2003), Wiley-VCH, Weinheim
9. Trnka T.M., and Grubbs R.H. Acc. Chem. Res. 34 (2001) 18-29
10. Fürstner A. Angew. Chem., Int. Ed. Engl. 39 (2000) 3012-3043
11. For a review on metathesis reactions in total syntheses see:. Nicolaou K.C., Bulger P.G., and Sarlah D. Angew Chem., Int. Ed. Engl. 44 (2005) 4490-4527
12. Zuercher W.J., Scholl M., and Grubbs R.H.J. Org. Chem. 63 (1998) 4291-4298
13. Kim S.-H., Zuercher W.J., Bowden N.B., and Grubbs R.H.J. Org. Chem. 61 (1996) 1073-1081
14. For a review see:. Randl S., and Blechert S. In: Grubbs R.H. (Ed). Handbook of Metathesis Vol. 2 (2003), Wiley-VCH, Weinheim 151-175
15. Schwab P., France M.B., Ziller J.W., and Grubbs R.H. Angew. Chem., Int. Ed. Engl. 34 (1995) 2039-2041
16. Scholl M., Ding S., Lee C.W., and Grubbs R.H. Org. Lett. 1 (1999) 953-956
17. For recent reviews on enyne metathesis, see:. Mori M. In: Grubbs R.H. (Ed). Handbook of Metathesis vol. 2 (2003), Wiley-VCH, Weinheim 176-204
18. Poulsen C.S., and Madsen R. Synthesis (2003) 1-18
19. Diver S.T., and Giessert A.J. Chem. Rev. 104 (2004) 1317-1382
20. For a recent article on the selectivity of RCM enyne metathesis see:. Hansen E.C., and Lee D.J. Am. Chem. Soc. 126 (2004) 15074-15080
21. For recent examples of synthesis of carbobicyclic systems by metathesis of dienynes, see:. Codesido E.M., Castedo L., and Granja J.R. Org. Lett. 3 (2001) 1483-1486
22. Garcia-Fandino R., Codesido E.M., Sobarzo-Sanchez E., Castedo L., and Granja J.R. Org. Lett. 6 (2004) 193-196
23. For recent examples of synthesis of heterobicyclic systems by metathesis of dienynes, see:. Choi T.-L., and Grubbs R. Chem. Commun. (2001) 2648-2649
24. Huang J., Xiong H., Hsung R.P., Rameshkumar C., Mulder J.A., and Grebe T.P. Org. Lett. 4 (2002) 2417-2420
25. Shimizu K., Takimoto M., and Mori M. Org. Lett. 5 (2003) 2323-2326
26. Wu C.-J., Madhushaw R.J., and Liu R.-S.J. Org. Chem. 68 (2003) 7889-7892
27. Honda T., Namiki H., Kaneda K., and Mizutani H. Org. Lett. 6 (2004) 87-89
28. Kaliappan K.P., and Nandurdikar R.S. Chem. Commun. (2004) 2506-2507
29. Fukumoto H., Takahashi K., Ishihara J., and Hatakeyama S. Angew. Chem., Int. Ed. Engl. 45 (2006) 2732-2734
30. For a review on group-selective ring-closing enyne metathesis see:. Maifeld S.V., and Lee D. Chem. Eur. J. 11 (2005) 6118-6126
31. Boyer F.-D., Hanna I., and Ricard L. Org. Lett. 3 (2001) 3095-3098
32. Boyer F.-D., Hanna I., and Ricard L. Org. Lett. 6 (2004) 1817-1820
33. Boyer F.-D., and Hanna I. Tetrahedron Lett. 43 (2002) 7469-7472
34. Boyer F.-D., and Hanna I. Eur. J. Org. Chem. (2006) 471-482
35. The preparation of dienynes 6-11 is described in the Supplementary Material.
36. For a recent report on olefin isomerization-ring-closing metathesis see:. Michalak M., and Wicha J. Synlett (2005) 2277-2280 and references cited
37. Boyer F.-D., and Hanna I. J. Org. Chem. 70 (2005) 1077-1080