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Volumn 606, Issue 1, 2000, Pages 75-78

Ring closing alkyne metathesis: Stereoselective synthesis of civetone

Author keywords

Alkylidynes; Alkynes; Macrocycles; Metathesis; Molybdenum; Tungsten

Indexed keywords


EID: 0037569978     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(00)00096-6     Document Type: Article
Times cited : (74)

References (40)
  • 1
    • 0032580376 scopus 로고    scopus 로고
    • Recent reviews: (a) R. H. Grubbs, S. Chang, Tetrahedron 54 (1998) 4413. (b) A. Fürstner, Top. Catal. 4 (1997) 285. M. Schuster, S. Blechert, Angew. Chem. Int. Ed. Engl. 36 (1997) 2036. A. Fürstner, Top. Organomet. Chem. 1 (1998) 37.
    • (1998) Tetrahedron , vol.54 , pp. 4413
    • Grubbs, R.H.1    Chang, S.2
  • 2
    • 0000522581 scopus 로고    scopus 로고
    • Recent reviews: (a) R. H. Grubbs, S. Chang, Tetrahedron 54 (1998) 4413. (b) A. Fürstner, Top. Catal. 4 (1997) 285. M. Schuster, S. Blechert, Angew. Chem. Int. Ed. Engl. 36 (1997) 2036. A. Fürstner, Top. Organomet. Chem. 1 (1998) 37.
    • (1997) Top. Catal. , vol.4 , pp. 285
    • Fürstner, A.1
  • 3
    • 0030771019 scopus 로고    scopus 로고
    • Recent reviews: (a) R. H. Grubbs, S. Chang, Tetrahedron 54 (1998) 4413. (b) A. Fürstner, Top. Catal. 4 (1997) 285. M. Schuster, S. Blechert, Angew. Chem. Int. Ed. Engl. 36 (1997) 2036. A. Fürstner, Top. Organomet. Chem. 1 (1998) 37.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 2036
    • Schuster, M.1    Blechert, S.2
  • 4
    • 0032580376 scopus 로고    scopus 로고
    • Recent reviews: (a) R. H. Grubbs, S. Chang, Tetrahedron 54 (1998) 4413. (b) A. Fürstner, Top. Catal. 4 (1997) 285. M. Schuster, S. Blechert, Angew. Chem. Int. Ed. Engl. 36 (1997) 2036. A. Fürstner, Top. Organomet. Chem. 1 (1998) 37.
    • (1998) Top. Organomet. Chem. , vol.1 , pp. 37
    • Fürstner, A.1
  • 8
    • 0030599269 scopus 로고    scopus 로고
    • For further examples from our laboratory illustrating this aspect see: (a) A. Fürstner, N. Kindler, Tetrahedron Lett. 37 (1996) 7005. (b) A. Fürstner, K. Langemann, J. Am. Chem. Soc. 119 (1997) 9130. A. Fürstner, K. Langemann, J. Org. Chem. 61 (1996) 8746. A. Fürstner, T. Müller, Synlett (1997) 1010. (e) A. Fürstner, T. Müller, J. Org. Chem. 63 (1998) 424. (f) A. Fürstner, T. Müller, J. Am. Chem. Soc. 121 (1999) 7814. (g) A. Fürstner, G. Seidel, N. Kindler, Tetrahedron 55 (1999) 8215. (h) A. Fürstner, T. Gastner, H. Weintritt, J. Org. Chem. 64 (1999) 2361. A. Fürstner, J. Grabowski, C. W. Lehmann, J. Org. Chem. 64 (1999) 8275.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7005
    • Fürstner, A.1    Kindler, N.2
  • 9
    • 0038163433 scopus 로고    scopus 로고
    • For further examples from our laboratory illustrating this aspect see: (a) A. Fürstner, N. Kindler, Tetrahedron Lett. 37 (1996) 7005. (b) A. Fürstner, K. Langemann, J. Am. Chem. Soc. 119 (1997) 9130. A. Fürstner, K. Langemann, J. Org. Chem. 61 (1996) 8746. A. Fürstner, T. Müller, Synlett (1997) 1010. (e) A. Fürstner, T. Müller, J. Org. Chem. 63 (1998) 424. (f) A. Fürstner, T. Müller, J. Am. Chem. Soc. 121 (1999) 7814. (g) A. Fürstner, G. Seidel, N. Kindler, Tetrahedron 55 (1999) 8215. (h) A. Fürstner, T. Gastner, H. Weintritt, J. Org. Chem. 64 (1999) 2361. A. Fürstner, J. Grabowski, C. W. Lehmann, J. Org. Chem. 64 (1999) 8275.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 9130
    • Fürstner, A.1    Langemann, K.2
  • 10
    • 0030443083 scopus 로고    scopus 로고
    • For further examples from our laboratory illustrating this aspect see: (a) A. Fürstner, N. Kindler, Tetrahedron Lett. 37 (1996) 7005. (b) A. Fürstner, K. Langemann, J. Am. Chem. Soc. 119 (1997) 9130. A. Fürstner, K. Langemann, J. Org. Chem. 61 (1996) 8746. A. Fürstner, T. Müller, Synlett (1997) 1010. (e) A. Fürstner, T. Müller, J. Org. Chem. 63 (1998) 424. (f) A. Fürstner, T. Müller, J. Am. Chem. Soc. 121 (1999) 7814. (g) A. Fürstner, G. Seidel, N. Kindler, Tetrahedron 55 (1999) 8215. (h) A. Fürstner, T. Gastner, H. Weintritt, J. Org. Chem. 64 (1999) 2361. A. Fürstner, J. Grabowski, C. W. Lehmann, J. Org. Chem. 64 (1999) 8275.
    • (1996) J. Org. Chem. , vol.61 , pp. 8746
    • Fürstner, A.1    Langemann, K.2
  • 11
    • 0037914291 scopus 로고    scopus 로고
    • For further examples from our laboratory illustrating this aspect see: (a) A. Fürstner, N. Kindler, Tetrahedron Lett. 37 (1996) 7005. (b) A. Fürstner, K. Langemann, J. Am. Chem. Soc. 119 (1997) 9130. A. Fürstner, K. Langemann, J. Org. Chem. 61 (1996) 8746. A. Fürstner, T. Müller, Synlett (1997) 1010. (e) A. Fürstner, T. Müller, J. Org. Chem. 63 (1998) 424. (f) A. Fürstner, T. Müller, J. Am. Chem. Soc. 121 (1999) 7814. (g) A. Fürstner, G. Seidel, N. Kindler, Tetrahedron 55 (1999) 8215. (h) A. Fürstner, T. Gastner, H. Weintritt, J. Org. Chem. 64 (1999) 2361. A. Fürstner, J. Grabowski, C. W. Lehmann, J. Org. Chem. 64 (1999) 8275.
    • (1997) Synlett , pp. 1010
    • Fürstner, A.1    Müller, T.2
  • 12
    • 0032489027 scopus 로고    scopus 로고
    • For further examples from our laboratory illustrating this aspect see: (a) A. Fürstner, N. Kindler, Tetrahedron Lett. 37 (1996) 7005. (b) A. Fürstner, K. Langemann, J. Am. Chem. Soc. 119 (1997) 9130. A. Fürstner, K. Langemann, J. Org. Chem. 61 (1996) 8746. A. Fürstner, T. Müller, Synlett (1997) 1010. (e) A. Fürstner, T. Müller, J. Org. Chem. 63 (1998) 424. (f) A. Fürstner, T. Müller, J. Am. Chem. Soc. 121 (1999) 7814. (g) A. Fürstner, G. Seidel, N. Kindler, Tetrahedron 55 (1999) 8215. (h) A. Fürstner, T. Gastner, H. Weintritt, J. Org. Chem. 64 (1999) 2361. A. Fürstner, J. Grabowski, C. W. Lehmann, J. Org. Chem. 64 (1999) 8275.
    • (1998) J. Org. Chem. , vol.63 , pp. 424
    • Fürstner, A.1    Müller, T.2
  • 13
    • 0038528214 scopus 로고    scopus 로고
    • For further examples from our laboratory illustrating this aspect see: (a) A. Fürstner, N. Kindler, Tetrahedron Lett. 37 (1996) 7005. (b) A. Fürstner, K. Langemann, J. Am. Chem. Soc. 119 (1997) 9130. A. Fürstner, K. Langemann, J. Org. Chem. 61 (1996) 8746. A. Fürstner, T. Müller, Synlett (1997) 1010. (e) A. Fürstner, T. Müller, J. Org. Chem. 63 (1998) 424. (f) A. Fürstner, T. Müller, J. Am. Chem. Soc. 121 (1999) 7814. (g) A. Fürstner, G. Seidel, N. Kindler, Tetrahedron 55 (1999) 8215. (h) A. Fürstner, T. Gastner, H. Weintritt, J. Org. Chem. 64 (1999) 2361. A. Fürstner, J. Grabowski, C. W. Lehmann, J. Org. Chem. 64 (1999) 8275.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 7814
    • Fürstner, A.1    Müller, T.2
  • 14
    • 0033516492 scopus 로고    scopus 로고
    • For further examples from our laboratory illustrating this aspect see: (a) A. Fürstner, N. Kindler, Tetrahedron Lett. 37 (1996) 7005. (b) A. Fürstner, K. Langemann, J. Am. Chem. Soc. 119 (1997) 9130. A. Fürstner, K. Langemann, J. Org. Chem. 61 (1996) 8746. A. Fürstner, T. Müller, Synlett (1997) 1010. (e) A. Fürstner, T. Müller, J. Org. Chem. 63 (1998) 424. (f) A. Fürstner, T. Müller, J. Am. Chem. Soc. 121 (1999) 7814. (g) A. Fürstner, G. Seidel, N. Kindler, Tetrahedron 55 (1999) 8215. (h) A. Fürstner, T. Gastner, H. Weintritt, J. Org. Chem. 64 (1999) 2361. A. Fürstner, J. Grabowski, C. W. Lehmann, J. Org. Chem. 64 (1999) 8275.
    • (1999) Tetrahedron , vol.55 , pp. 8215
    • Fürstner, A.1    Seidel, G.2    Kindler, N.3
  • 15
    • 0033515494 scopus 로고    scopus 로고
    • For further examples from our laboratory illustrating this aspect see: (a) A. Fürstner, N. Kindler, Tetrahedron Lett. 37 (1996) 7005. (b) A. Fürstner, K. Langemann, J. Am. Chem. Soc. 119 (1997) 9130. A. Fürstner, K. Langemann, J. Org. Chem. 61 (1996) 8746. A. Fürstner, T. Müller, Synlett (1997) 1010. (e) A. Fürstner, T. Müller, J. Org. Chem. 63 (1998) 424. (f) A. Fürstner, T. Müller, J. Am. Chem. Soc. 121 (1999) 7814. (g) A. Fürstner, G. Seidel, N. Kindler, Tetrahedron 55 (1999) 8215. (h) A. Fürstner, T. Gastner, H. Weintritt, J. Org. Chem. 64 (1999) 2361. A. Fürstner, J. Grabowski, C. W. Lehmann, J. Org. Chem. 64 (1999) 8275.
    • (1999) J. Org. Chem. , vol.64 , pp. 2361
    • Fürstner, A.1    Gastner, T.2    Weintritt, H.3
  • 16
    • 0038590297 scopus 로고    scopus 로고
    • For further examples from our laboratory illustrating this aspect see: (a) A. Fürstner, N. Kindler, Tetrahedron Lett. 37 (1996) 7005. (b) A. Fürstner, K. Langemann, J. Am. Chem. Soc. 119 (1997) 9130. A. Fürstner, K. Langemann, J. Org. Chem. 61 (1996) 8746. A. Fürstner, T. Müller, Synlett (1997) 1010. (e) A. Fürstner, T. Müller, J. Org. Chem. 63 (1998) 424. (f) A. Fürstner, T. Müller, J. Am. Chem. Soc. 121 (1999) 7814. (g) A. Fürstner, G. Seidel, N. Kindler, Tetrahedron 55 (1999) 8215. (h) A. Fürstner, T. Gastner, H. Weintritt, J. Org. Chem. 64 (1999) 2361. A. Fürstner, J. Grabowski, C. W. Lehmann, J. Org. Chem. 64 (1999) 8275.
    • (1999) J. Org. Chem. , vol.64 , pp. 8275
    • Fürstner, A.1    Grabowski, J.2    Lehmann, C.W.3
  • 17
    • 0003963554 scopus 로고
    • Springer, Berlin
    • For reviews see: (a) G. Ohloff, Riechstoffe und Geruchssinn, Springer, Berlin 1990. (b) K. Bauer, D. Garbe, H. Surburg, in: Ullmann's Encyclopedia of Industrial Chemistry, fifth ed., vol. A11, VCH, Weinheim, 1988, p. 141. A. S. Williams, Synthesis (1999) 1707. G. Fráter, J.A. Bajgrowicz, P. Kraft, Tetrahedron 54 (1998) 7633.
    • (1990) Riechstoffe und Geruchssinn
    • Ohloff, G.1
  • 18
    • 0001531345 scopus 로고
    • VCH, Weinheim
    • For reviews see: (a) G. Ohloff, Riechstoffe und Geruchssinn, Springer, Berlin 1990. (b) K. Bauer, D. Garbe, H. Surburg, in: Ullmann's Encyclopedia of Industrial Chemistry, fifth ed., vol. A11, VCH, Weinheim, 1988, p. 141. A. S. Williams, Synthesis (1999) 1707. G. Fráter, J.A. Bajgrowicz, P. Kraft, Tetrahedron 54 (1998) 7633.
    • (1988) Ullmann's Encyclopedia of Industrial Chemistry, Fifth Ed. , vol.A11 , pp. 141
    • Bauer, K.1    Garbe, D.2    Surburg, H.3
  • 19
    • 0032870907 scopus 로고    scopus 로고
    • For reviews see: (a) G. Ohloff, Riechstoffe und Geruchssinn, Springer, Berlin 1990. (b) K. Bauer, D. Garbe, H. Surburg, in: Ullmann's Encyclopedia of Industrial Chemistry, fifth ed., vol. A11, VCH, Weinheim, 1988, p. 141. A. S. Williams, Synthesis (1999) 1707. G. Fráter, J.A. Bajgrowicz, P. Kraft, Tetrahedron 54 (1998) 7633.
    • (1999) Synthesis , pp. 1707
    • Williams, A.S.1
  • 20
    • 0032474807 scopus 로고    scopus 로고
    • For reviews see: (a) G. Ohloff, Riechstoffe und Geruchssinn, Springer, Berlin 1990. (b) K. Bauer, D. Garbe, H. Surburg, in: Ullmann's Encyclopedia of Industrial Chemistry, fifth ed., vol. A11, VCH, Weinheim, 1988, p. 141. A. S. Williams, Synthesis (1999) 1707. G. Fráter, J.A. Bajgrowicz, P. Kraft, Tetrahedron 54 (1998) 7633.
    • (1998) Tetrahedron , vol.54 , pp. 7633
    • Fráter, G.1    Bajgrowicz, J.A.2    Kraft, P.3
  • 21
  • 22
    • 0038731101 scopus 로고    scopus 로고
    • (a) A. Fürstner, G. Seidel, Angew. Chem. 110 (1998) 1758; Angew. Chem. Int. Ed. Engl. 37 (1998) 1734.
    • (1998) Angew. Chem. Int. Ed. Engl. , vol.37 , pp. 1734
  • 29
    • 0000868831 scopus 로고
    • 3 (R = 2,6-diisopropylphenyl) is reported to react rapidly with acetone, benzaldehyde, paraformaldehyde, ethyl formate, DMF and acetonitrile in Wittig-like reactions, cf.: J.H. Freudenberger, R.R. Schrock, Organometallics 5 (1986) 398.
    • (1986) Organometallics , vol.5 , pp. 398
    • Freudenberger, J.H.1    Schrock, R.R.2
  • 30
    • 37049120275 scopus 로고
    • 6 and phenol additives has been originally proposed as alkyne metathesis catalyst by Mortreux et al, cf.: (a) A. Mortreux, M. Blanchard, J. Chem. Soc. Chem. Commun. (1974) 786. (b) A. Mortreux, N. Dy, M. Blanchard, J. Mol. Catal. 1 (1975) 101. A. Mortreux, J.C. Delgrange, M. Blanchard, B. Lubochinsky, J. Mol. Catal. 2 (1977) 73. For comments on the reactive intermediates formed under these conditions see: L.G. McCullough, R.R. Schrock, J. Am. Chem. Soc. 106 (1984) 4067.
    • (1974) J. Chem. Soc. Chem. Commun. , pp. 786
    • Mortreux, A.1    Blanchard, M.2
  • 31
    • 0001391591 scopus 로고
    • 6 and phenol additives has been originally proposed as alkyne metathesis catalyst by Mortreux et al, cf.: (a) A. Mortreux, M. Blanchard, J. Chem. Soc. Chem. Commun. (1974) 786. (b) A. Mortreux, N. Dy, M. Blanchard, J. Mol. Catal. 1 (1975) 101. A. Mortreux, J.C. Delgrange, M. Blanchard, B. Lubochinsky, J. Mol. Catal. 2 (1977) 73. For comments on the reactive intermediates formed under these conditions see: L.G. McCullough, R.R. Schrock, J. Am. Chem. Soc. 106 (1984) 4067.
    • (1975) J. Mol. Catal. , vol.1 , pp. 101
    • Mortreux, A.1    Dy, N.2    Blanchard, M.3
  • 32
    • 0001865966 scopus 로고
    • 6 and phenol additives has been originally proposed as alkyne metathesis catalyst by Mortreux et al, cf.: (a) A. Mortreux, M. Blanchard, J. Chem. Soc. Chem. Commun. (1974) 786. (b) A. Mortreux, N. Dy, M. Blanchard, J. Mol. Catal. 1 (1975) 101. A. Mortreux, J.C. Delgrange, M. Blanchard, B. Lubochinsky, J. Mol. Catal. 2 (1977) 73. For comments on the reactive intermediates formed under these conditions see: L.G. McCullough, R.R. Schrock, J. Am. Chem. Soc. 106 (1984) 4067.
    • (1977) J. Mol. Catal. , vol.2 , pp. 73
    • Mortreux, A.1    Delgrange, J.C.2    Blanchard, M.3    Lubochinsky, B.4
  • 33
    • 0342847826 scopus 로고
    • 6 and phenol additives has been originally proposed as alkyne metathesis catalyst by Mortreux et al, cf.: (a) A. Mortreux, M. Blanchard, J. Chem. Soc. Chem. Commun. (1974) 786. (b) A. Mortreux, N. Dy, M. Blanchard, J. Mol. Catal. 1 (1975) 101. A. Mortreux, J.C. Delgrange, M. Blanchard, B. Lubochinsky, J. Mol. Catal. 2 (1977) 73. For comments on the reactive intermediates formed under these conditions see: L.G. McCullough, R.R. Schrock, J. Am. Chem. Soc. 106 (1984) 4067.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 4067
    • McCullough, L.G.1    Schrock, R.R.2
  • 34
    • 0001395112 scopus 로고
    • For applications of the Mortreux system see: (a) D. Villemin, P. Cadiot, Tetrahedron Lett. 23 (1982) 5139. (b) J.A.K. Du Plessis, H.C.M. Vosloo, J. Mol. Catal. 65 (1991) 51. N. Kaneta, T. Hirai, M. Mori, Chem. Lett. (1995) 627. N. Kaneta, K. Hikichi, S.-I. Asaka, M. Uemura, M. Mori, Chem. Lett. (1995) 1055.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 5139
    • Villemin, D.1    Cadiot, P.2
  • 35
    • 0026124173 scopus 로고
    • For applications of the Mortreux system see: (a) D. Villemin, P. Cadiot, Tetrahedron Lett. 23 (1982) 5139. (b) J.A.K. Du Plessis, H.C.M. Vosloo, J. Mol. Catal. 65 (1991) 51. N. Kaneta, T. Hirai, M. Mori, Chem. Lett. (1995) 627. N. Kaneta, K. Hikichi, S.-I. Asaka, M. Uemura, M. Mori, Chem. Lett. (1995) 1055.
    • (1991) J. Mol. Catal. , vol.65 , pp. 51
    • Du Plessis, J.A.K.1    Vosloo, H.C.M.2
  • 36
    • 0001395112 scopus 로고
    • For applications of the Mortreux system see: (a) D. Villemin, P. Cadiot, Tetrahedron Lett. 23 (1982) 5139. (b) J.A.K. Du Plessis, H.C.M. Vosloo, J. Mol. Catal. 65 (1991) 51. N. Kaneta, T. Hirai, M. Mori, Chem. Lett. (1995) 627. N. Kaneta, K. Hikichi, S.-I. Asaka, M. Uemura, M. Mori, Chem. Lett. (1995) 1055.
    • (1995) Chem. Lett. , pp. 627
    • Kaneta, N.1    Hirai, T.2    Mori, M.3
  • 37
    • 0001395112 scopus 로고
    • For applications of the Mortreux system see: (a) D. Villemin, P. Cadiot, Tetrahedron Lett. 23 (1982) 5139. (b) J.A.K. Du Plessis, H.C.M. Vosloo, J. Mol. Catal. 65 (1991) 51. N. Kaneta, T. Hirai, M. Mori, Chem. Lett. (1995) 627. N. Kaneta, K. Hikichi, S.-I. Asaka, M. Uemura, M. Mori, Chem. Lett. (1995) 1055.
    • (1995) Chem. Lett. , pp. 1055
    • Kaneta, N.1    Hikichi, K.2    Asaka, S.-I.3    Uemura, M.4    Mori, M.5
  • 38
    • 0032511426 scopus 로고    scopus 로고
    • For further optimizations and applications see: (a) L. Kloppen-burg, D. Song, U.H.F. Bunz, J. Am. Chem. Soc. 120 (1998) 7973. (b) N.G. Pschirer, U.H.F. Bunz, Tetrahedron Lett. 40 (1999) 2481.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 7973
    • Kloppen-burg, L.1    Song, D.2    Bunz, U.H.F.3
  • 39
    • 0033605877 scopus 로고    scopus 로고
    • For further optimizations and applications see: (a) L. Kloppen- burg, D. Song, U.H.F. Bunz, J. Am. Chem. Soc. 120 (1998) 7973. (b) N.G. Pschirer, U.H.F. Bunz, Tetrahedron Lett. 40 (1999) 2481.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 2481
    • Pschirer, N.G.1    Bunz, U.H.F.2
  • 40
    • 0038542691 scopus 로고    scopus 로고
    • For an account on our objectives in catalysis based synthesis see: A. Fürstner, Synlett (1999) 1523.
    • (1999) Synlett , pp. 1523
    • Fürstner, A.1


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