Sequential Michael Addition-Carbocyclization Reactions: A Palladium-Mediated Approach to Highly Functionalized 3-Methylenetetrahydrofurans

Synlett

Volumn 1997, Issue 7, 1997, Pages 845-847

  Marat, Xavier ^a   Monteiro, Nuno ^a   Balme, Geneviève ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000541824     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-5755     Document Type: Article

References (27)

1. Doblem, M. Ionophores and Their Structures; Wiley-Interscience New York, 1981. Westley, J.W., Ed. Polyether Antibiotics ; Marcel Dekker: New York, 1982; Vols. I and II. Erickson, K.L. In Marine Natural Products ; Scheuer, P.J., Ed. Academic Press: New York, 1983; Vol. 5, Chapter 4, 131. Boivin, T.L.B. Tetrahedron 1987, 43, 3309. Moody, C.J.; Davies, M. In Studies in Natural Product Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam 1992, Vol. 10, 201. Harmange, J.-C.; Figadère, B. Tetrahedron Asymmetry 1993, 4, 1711. Alvarez, E.; Candenas, M.-L.; Pérez, R.; Ravelo, J. L.; Martin, J. D. Chem. Rev. 1995, 95, 1953.
2. Doblem, M. Ionophores and Their Structures; Wiley-Interscience New York, 1981. Westley, J.W., Ed. Polyether Antibiotics ; Marcel Dekker: New York, 1982; Vols. I and II. Erickson, K.L. In Marine Natural Products ; Scheuer, P.J., Ed. Academic Press: New York, 1983; Vol. 5, Chapter 4, 131. Boivin, T.L.B. Tetrahedron 1987, 43, 3309. Moody, C.J.; Davies, M. In Studies in Natural Product Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam 1992, Vol. 10, 201. Harmange, J.-C.; Figadère, B. Tetrahedron Asymmetry 1993, 4, 1711. Alvarez, E.; Candenas, M.-L.; Pérez, R.; Ravelo, J. L.; Martin, J. D. Chem. Rev. 1995, 95, 1953.
3. Doblem, M. Ionophores and Their Structures; Wiley-Interscience New York, 1981. Westley, J.W., Ed. Polyether Antibiotics ; Marcel Dekker: New York, 1982; Vols. I and II. Erickson, K.L. In Marine Natural Products ; Scheuer, P.J., Ed. Academic Press: New York, 1983; Vol. 5, Chapter 4, 131. Boivin, T.L.B. Tetrahedron 1987, 43, 3309. Moody, C.J.; Davies, M. In Studies in Natural Product Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam 1992, Vol. 10, 201. Harmange, J.-C.; Figadère, B. Tetrahedron Asymmetry 1993, 4, 1711. Alvarez, E.; Candenas, M.-L.; Pérez, R.; Ravelo, J. L.; Martin, J. D. Chem. Rev. 1995, 95, 1953.
4. Doblem, M. Ionophores and Their Structures; Wiley-Interscience New York, 1981. Westley, J.W., Ed. Polyether Antibiotics ; Marcel Dekker: New York, 1982; Vols. I and II. Erickson, K.L. In Marine Natural Products ; Scheuer, P.J., Ed. Academic Press: New York, 1983; Vol. 5, Chapter 4, 131. Boivin, T.L.B. Tetrahedron 1987, 43, 3309. Moody, C.J.; Davies, M. In Studies in Natural Product Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam 1992, Vol. 10, 201. Harmange, J.-C.; Figadère, B. Tetrahedron Asymmetry 1993, 4, 1711. Alvarez, E.; Candenas, M.-L.; Pérez, R.; Ravelo, J. L.; Martin, J. D. Chem. Rev. 1995, 95, 1953.
5. Doblem, M. Ionophores and Their Structures; Wiley-Interscience New York, 1981. Westley, J.W., Ed. Polyether Antibiotics ; Marcel Dekker: New York, 1982; Vols. I and II. Erickson, K.L. In Marine Natural Products ; Scheuer, P.J., Ed. Academic Press: New York, 1983; Vol. 5, Chapter 4, 131. Boivin, T.L.B. Tetrahedron 1987, 43, 3309. Moody, C.J.; Davies, M. In Studies in Natural Product Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam 1992, Vol. 10, 201. Harmange, J.-C.; Figadère, B. Tetrahedron Asymmetry 1993, 4, 1711. Alvarez, E.; Candenas, M.-L.; Pérez, R.; Ravelo, J. L.; Martin, J. D. Chem. Rev. 1995, 95, 1953.
6. Doblem, M. Ionophores and Their Structures; Wiley-Interscience New York, 1981. Westley, J.W., Ed. Polyether Antibiotics ; Marcel Dekker: New York, 1982; Vols. I and II. Erickson, K.L. In Marine Natural Products ; Scheuer, P.J., Ed. Academic Press: New York, 1983; Vol. 5, Chapter 4, 131. Boivin, T.L.B. Tetrahedron 1987, 43, 3309. Moody, C.J.; Davies, M. In Studies in Natural Product Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam 1992, Vol. 10, 201. Harmange, J.-C.; Figadère, B. Tetrahedron Asymmetry 1993, 4, 1711. Alvarez, E.; Candenas, M.-L.; Pérez, R.; Ravelo, J. L.; Martin, J. D. Chem. Rev. 1995, 95, 1953.
7. Doblem, M. Ionophores and Their Structures; Wiley-Interscience New York, 1981. Westley, J.W., Ed. Polyether Antibiotics ; Marcel Dekker: New York, 1982; Vols. I and II. Erickson, K.L. In Marine Natural Products ; Scheuer, P.J., Ed. Academic Press: New York, 1983; Vol. 5, Chapter 4, 131. Boivin, T.L.B. Tetrahedron 1987, 43, 3309. Moody, C.J.; Davies, M. In Studies in Natural Product Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam 1992, Vol. 10, 201. Harmange, J.-C.; Figadère, B. Tetrahedron Asymmetry 1993, 4, 1711. Alvarez, E.; Candenas, M.-L.; Pérez, R.; Ravelo, J. L.; Martin, J. D. Chem. Rev. 1995, 95, 1953.
8. Giese, B. Radicals in Organic Synthesis : Formation of Carbon Carbon Bonds; Pergamon Press: Oxford 1986. Burke, S.D., Jung, K.W. Tetrahedron Lett. 1994, 35, 5837 and references cited therein.
9. Giese, B. Radicals in Organic Synthesis : Formation of Carbon Carbon Bonds; Pergamon Press: Oxford 1986. Burke, S.D., Jung, K.W. Tetrahedron Lett. 1994, 35, 5837 and references cited therein.
10. Tsuji, J. Palladium Reagents and Catalysts : Innovations in Organic Synthesis John Wiley & Sons, Chichester 1995.
11. Monteiro, N. ; Goré, J.; Balme, G. Tetrahedron 1992, 48, 10103. α-Sulfonyl ε-acetylenic esters, nitriles and ketones behaved differently in these reactions: See Monteiro, N.; Balme, G.; Goré, J. Synlett 1992, 227. Monteiro, N.; Goré, J.; Van Hemelryck, B.; Balme, G. Synlett 1994, 447.
12. Monteiro, N. ; Goré, J.; Balme, G. Tetrahedron 1992, 48, 10103. α-Sulfonyl ε-acetylenic esters, nitriles and ketones behaved differently in these reactions: See Monteiro, N.; Balme, G.; Goré, J. Synlett 1992, 227. Monteiro, N.; Goré, J.; Van Hemelryck, B.; Balme, G. Synlett 1994, 447.
13. Monteiro, N. ; Goré, J.; Balme, G. Tetrahedron 1992, 48, 10103. α-Sulfonyl ε-acetylenic esters, nitriles and ketones behaved differently in these reactions: See Monteiro, N.; Balme, G.; Goré, J. Synlett 1992, 227. Monteiro, N.; Goré, J.; Van Hemelryck, B.; Balme, G. Synlett 1994, 447.
14. Trost, B.M.; Chan, C; Rüther, G. J. Am. Chem. Soc. 1987, 109, 3486 and references cited therein. Trost, B.M.; Sorum, M.T.; Chan, C; Harms, A.E.; Rüther, G. J. Am. Chem. Soc. 1997, 119, 698. See also Grushin, V.V. Chem. Rev. 1996, 96, 2011.
15. Trost, B.M.; Chan, C; Rüther, G. J. Am. Chem. Soc. 1987, 109, 3486 and references cited therein. Trost, B.M.; Sorum, M.T.; Chan, C; Harms, A.E.; Rüther, G. J. Am. Chem. Soc. 1997, 119, 698. See also Grushin, V.V. Chem. Rev. 1996, 96, 2011.
16. Trost, B.M.; Chan, C; Rüther, G. J. Am. Chem. Soc. 1987, 109, 3486 and references cited therein. Trost, B.M.; Sorum, M.T.; Chan, C; Harms, A.E.; Rüther, G. J. Am. Chem. Soc. 1997, 119, 698. See also Grushin, V.V. Chem. Rev. 1996, 96, 2011.
17. For representative recent examples of 3-methylenetetrahydrofuran syntheses see: Maiti, G.; Adhikari, S.; Roy, S.C. Tetrahedron 1995, 51, 8389. Van der Baan, J.L.; Van der Heide, T.A.J.; Van der Louw, J.; Klumpp, G.W. Synlett 1995, 1 and references cited therein. Gordaliza, M.; Miguel del Corral, J.M.; Castro, M.A.; Salinero, M.A.; San Feliciano, A.; Dorado, J.M.; Valle, F. Synlett 1996, 1201.
18. For representative recent examples of 3-methylenetetrahydrofuran syntheses see: Maiti, G.; Adhikari, S.; Roy, S.C. Tetrahedron 1995, 51, 8389. Van der Baan, J.L.; Van der Heide, T.A.J.; Van der Louw, J.; Klumpp, G.W. Synlett 1995, 1 and references cited therein. Gordaliza, M.; Miguel del Corral, J.M.; Castro, M.A.; Salinero, M.A.; San Feliciano, A.; Dorado, J.M.; Valle, F. Synlett 1996, 1201.
19. For representative recent examples of 3-methylenetetrahydrofuran syntheses see: Maiti, G.; Adhikari, S.; Roy, S.C. Tetrahedron 1995, 51, 8389. Van der Baan, J.L.; Van der Heide, T.A.J.; Van der Louw, J.; Klumpp, G.W. Synlett 1995, 1 and references cited therein. Gordaliza, M.; Miguel del Corral, J.M.; Castro, M.A.; Salinero, M.A.; San Feliciano, A.; Dorado, J.M.; Valle, F. Synlett 1996, 1201.
20. Oxygen nucleophile initiated Michael additions have received only little attention. For examples see a) Bradley, H.M.; Knight, D.W. J. Chem. Soc., Chem. Commun. 1991, 1641.
21. b) Duffy, J.L.; Kurth, J.A.; Kurth, M.J. Tetrahedron Lett. 1993, 34, 1259.
22. c) Yakura, T.; Tsuda, T.; Matsumura, Y.; Yamada, S.; Ikeda, M. Synlett 1996, 985.
23. Cavicchioli, M.; Sixdenier, E.; Derrey, A.; Bouyssi , D.; Balme, G. Tetrahedron Lett. 1997, 38 , 1763.
24. 4 which showed poor reactivity.
25. 3 in 1 ml of the solvent. Stirring was continued until the Michael acceptor disappeared as determined by GC (1-10 hours). The solvent was then removed in vacuo and the residue was purified by flash chromatography on silica gel to give the pure tetrahydrofuran.
26. See Ward, R.S. Nat. Prod. Reports 1995, 183 and references cited therein.
27. Smith III, A.B.; Empfield, J.R. ; Rivero, R.A ; Vaccaro, H.A ; Duan, J.J.-W; Sulikowski, M.M. J. Am. Chem. Soc. 1992, 114, 9419.