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Volumn 61, Issue 18, 1996, Pages 6162-6165

Synthesis of bicyclic enediynes from bis[phenyl[(trifluoromethanesulfonyl)oxy]iodo]acetylene: A tandem Diels-Alder/palladium(II)- and copper(I)-cocatalyzed cross-coupling approach

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; NORBORNANE DERIVATIVE;

EID: 0029843695     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960750k     Document Type: Article
Times cited : (46)

References (60)
  • 1
    • 0030069884 scopus 로고    scopus 로고
    • For recent reviews: (a) Danishefsky, S. J.; Shair, M. D. J. Org. Chem. 1996, 61, 16. (b) Nicoloau, K. C.; Smith, A. L. in Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; Chapter 7. (b) Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1993, 32, 1377. (c) Pratveil, G.; Bernardou, J.; Meunier, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 746. (d) Magnus, P. Tetrahedron 1994, 50, 1397. Part of Tetrahedron's Symposia-in-print No. 53. Doyle, T. W., Kadow, J. F., Eds.; Tetrahedron 1994, 50, 1311-1538. (e) Thebtaranonth, C.; Thebtaranonth, Y. Cydization Reactions; CRC: Boca Raton, FL, 1994; pp 346-357.
    • (1996) J. Org. Chem. , vol.61 , pp. 16
    • Danishefsky, S.J.1    Shair, M.D.2
  • 2
    • 3643055431 scopus 로고
    • Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, Chapter 7
    • For recent reviews: (a) Danishefsky, S. J.; Shair, M. D. J. Org. Chem. 1996, 61, 16. (b) Nicoloau, K. C.; Smith, A. L. in Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; Chapter 7. (b) Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1993, 32, 1377. (c) Pratveil, G.; Bernardou, J.; Meunier, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 746. (d) Magnus, P. Tetrahedron 1994, 50, 1397. Part of Tetrahedron's Symposia-in-print No. 53. Doyle, T. W., Kadow, J. F., Eds.; Tetrahedron 1994, 50, 1311-1538. (e) Thebtaranonth, C.; Thebtaranonth, Y. Cydization Reactions; CRC: Boca Raton, FL, 1994; pp 346-357.
    • (1995) Modern Acetylene Chemistry
    • Nicoloau, K.C.1    Smith, A.L.2
  • 3
    • 33748828652 scopus 로고
    • For recent reviews: (a) Danishefsky, S. J.; Shair, M. D. J. Org. Chem. 1996, 61, 16. (b) Nicoloau, K. C.; Smith, A. L. in Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; Chapter 7. (b) Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1993, 32, 1377. (c) Pratveil, G.; Bernardou, J.; Meunier, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 746. (d) Magnus, P. Tetrahedron 1994, 50, 1397. Part of Tetrahedron's Symposia-in-print No. 53. Doyle, T. W., Kadow, J. F., Eds.; Tetrahedron 1994, 50, 1311-1538. (e) Thebtaranonth, C.; Thebtaranonth, Y. Cydization Reactions; CRC: Boca Raton, FL, 1994; pp 346-357.
    • (1993) Angew. Chem., Int. Ed. Engl. , vol.32 , pp. 1377
    • Nicolaou, K.C.1
  • 4
    • 0029103994 scopus 로고
    • For recent reviews: (a) Danishefsky, S. J.; Shair, M. D. J. Org. Chem. 1996, 61, 16. (b) Nicoloau, K. C.; Smith, A. L. in Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; Chapter 7. (b) Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1993, 32, 1377. (c) Pratveil, G.; Bernardou, J.; Meunier, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 746. (d) Magnus, P. Tetrahedron 1994, 50, 1397. Part of Tetrahedron's Symposia-in-print No. 53. Doyle, T. W., Kadow, J. F., Eds.; Tetrahedron 1994, 50, 1311-1538. (e) Thebtaranonth, C.; Thebtaranonth, Y. Cydization Reactions; CRC: Boca Raton, FL, 1994; pp 346-357.
    • (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 746
    • Pratveil, G.1    Bernardou, J.2    Meunier, B.3
  • 5
    • 0027979271 scopus 로고
    • For recent reviews: (a) Danishefsky, S. J.; Shair, M. D. J. Org. Chem. 1996, 61, 16. (b) Nicoloau, K. C.; Smith, A. L. in Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; Chapter 7. (b) Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1993, 32, 1377. (c) Pratveil, G.; Bernardou, J.; Meunier, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 746. (d) Magnus, P. Tetrahedron 1994, 50, 1397. Part of Tetrahedron's Symposia-in-print No. 53. Doyle, T. W., Kadow, J. F., Eds.; Tetrahedron 1994, 50, 1311-1538. (e) Thebtaranonth, C.; Thebtaranonth, Y. Cydization Reactions; CRC: Boca Raton, FL, 1994; pp 346-357.
    • (1994) Tetrahedron , vol.50 , pp. 1397
    • Magnus, P.1
  • 6
    • 0010555156 scopus 로고
    • For recent reviews: (a) Danishefsky, S. J.; Shair, M. D. J. Org. Chem. 1996, 61, 16. (b) Nicoloau, K. C.; Smith, A. L. in Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; Chapter 7. (b) Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1993, 32, 1377. (c) Pratveil, G.; Bernardou, J.; Meunier, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 746. (d) Magnus, P. Tetrahedron 1994, 50, 1397. Part of Tetrahedron's Symposia-in-print No. 53. Doyle, T. W., Kadow, J. F., Eds.; Tetrahedron 1994, 50, 1311-1538. (e) Thebtaranonth, C.; Thebtaranonth, Y. Cydization Reactions; CRC: Boca Raton, FL, 1994; pp 346-357.
    • (1994) Tetrahedron , vol.50 , pp. 1311-1538
    • Doyle, T.W.1    Kadow, J.F.2
  • 7
    • 0004209413 scopus 로고
    • CRC: Boca Raton, FL
    • For recent reviews: (a) Danishefsky, S. J.; Shair, M. D. J. Org. Chem. 1996, 61, 16. (b) Nicoloau, K. C.; Smith, A. L. in Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; Chapter 7. (b) Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1993, 32, 1377. (c) Pratveil, G.; Bernardou, J.; Meunier, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 746. (d) Magnus, P. Tetrahedron 1994, 50, 1397. Part of Tetrahedron's Symposia-in-print No. 53. Doyle, T. W., Kadow, J. F., Eds.; Tetrahedron 1994, 50, 1311-1538. (e) Thebtaranonth, C.; Thebtaranonth, Y. Cydization Reactions; CRC: Boca Raton, FL, 1994; pp 346-357.
    • (1994) Cydization Reactions , pp. 346-357
    • Thebtaranonth, C.1    Thebtaranonth, Y.2
  • 9
    • 0001555364 scopus 로고
    • For other early observations of the cyclizaaon of enediynes see: (b) Mayer, J.; Sondheimer, F. J. Am. Chem. Soc. 1966, 88, 603. (c) Darby, N.; Kim, C. U.; Salaün, J. A.; Shelton, K. W.; Takada, S.; Masamune, S. J. Chem. Soc., Chem. Commun. 1971, 1516.
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 603
    • Mayer, J.1    Sondheimer, F.2
  • 28
  • 30
    • 0028225955 scopus 로고
    • For recent examples that deal with the introduction of novel acetylenic side chains: (a) König, B.; Rütters, H. Tetrahedron Lett. 1994, 35, 3501. (b) Alami, M.; Crousse, B.; Linstrumelle, G. Tetrahedron Lett. 1994, 35, 3543. (c) McGaffin, G.; de Meijere, A. Synthesis 1994, 583. (d) Stracker, E. C.; Zweifel, G. Tetrahedron Lett. 1991, 32, 3329. (e) Magriotis, P. A.; Scott, M. E.; Kim, K. D. Tetrahedron Lett. 1991, 32, 6085.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 3501
    • König, B.1    Rütters, H.2
  • 31
    • 0028276499 scopus 로고
    • For recent examples that deal with the introduction of novel acetylenic side chains: (a) König, B.; Rütters, H. Tetrahedron Lett. 1994, 35, 3501. (b) Alami, M.; Crousse, B.; Linstrumelle, G. Tetrahedron Lett. 1994, 35, 3543. (c) McGaffin, G.; de Meijere, A. Synthesis 1994, 583. (d) Stracker, E. C.; Zweifel, G. Tetrahedron Lett. 1991, 32, 3329. (e) Magriotis, P. A.; Scott, M. E.; Kim, K. D. Tetrahedron Lett. 1991, 32, 6085.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 3543
    • Alami, M.1    Crousse, B.2    Linstrumelle, G.3
  • 32
    • 0028306543 scopus 로고
    • For recent examples that deal with the introduction of novel acetylenic side chains: (a) König, B.; Rütters, H. Tetrahedron Lett. 1994, 35, 3501. (b) Alami, M.; Crousse, B.; Linstrumelle, G. Tetrahedron Lett. 1994, 35, 3543. (c) McGaffin, G.; de Meijere, A. Synthesis 1994, 583. (d) Stracker, E. C.; Zweifel, G. Tetrahedron Lett. 1991, 32, 3329. (e) Magriotis, P. A.; Scott, M. E.; Kim, K. D. Tetrahedron Lett. 1991, 32, 6085.
    • (1994) Synthesis , pp. 583
    • McGaffin, G.1    De Meijere, A.2
  • 33
    • 0025896451 scopus 로고
    • For recent examples that deal with the introduction of novel acetylenic side chains: (a) König, B.; Rütters, H. Tetrahedron Lett. 1994, 35, 3501. (b) Alami, M.; Crousse, B.; Linstrumelle, G. Tetrahedron Lett. 1994, 35, 3543. (c) McGaffin, G.; de Meijere, A. Synthesis 1994, 583. (d) Stracker, E. C.; Zweifel, G. Tetrahedron Lett. 1991, 32, 3329. (e) Magriotis, P. A.; Scott, M. E.; Kim, K. D. Tetrahedron Lett. 1991, 32, 6085.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 3329
    • Stracker, E.C.1    Zweifel, G.2
  • 34
    • 0025945137 scopus 로고
    • For recent examples that deal with the introduction of novel acetylenic side chains: (a) König, B.; Rütters, H. Tetrahedron Lett. 1994, 35, 3501. (b) Alami, M.; Crousse, B.; Linstrumelle, G. Tetrahedron Lett. 1994, 35, 3543. (c) McGaffin, G.; de Meijere, A. Synthesis 1994, 583. (d) Stracker, E. C.; Zweifel, G. Tetrahedron Lett. 1991, 32, 3329. (e) Magriotis, P. A.; Scott, M. E.; Kim, K. D. Tetrahedron Lett. 1991, 32, 6085.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 6085
    • Magriotis, P.A.1    Scott, M.E.2    Kim, K.D.3
  • 35
    • 85033816084 scopus 로고    scopus 로고
    • in press
    • Reviews: (a) Stang, P. J.; Zhdankin, V. V. Chem. Rev., in press. (b) Koser, G. F. In The Chemistry of Halides, Pseudo-Halides and Azides, Suppl. D2; Patai, S., Rappoport, Z., Eds.; Wiley-Interscience: Chichester, 1995; Chapter 21, pp 1173-1274. (c) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992.
    • Chem. Rev.
    • Stang, P.J.1    Zhdankin, V.V.2
  • 36
    • 0002078016 scopus 로고
    • Patai, S., Rappoport, Z., Eds.; Wiley-Interscience: Chichester, Chapter 21
    • Reviews: (a) Stang, P. J.; Zhdankin, V. V. Chem. Rev., in press. (b) Koser, G. F. In The Chemistry of Halides, Pseudo-Halides and Azides, Suppl. D2; Patai, S., Rappoport, Z., Eds.; Wiley-Interscience: Chichester, 1995; Chapter 21, pp 1173-1274. (c) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992.
    • (1995) The Chemistry of Halides, Pseudo-Halides and Azides, Suppl. D2 , pp. 1173-1274
    • Koser, G.F.1
  • 37
    • 0003410653 scopus 로고
    • VCH Publishers: New York
    • Reviews: (a) Stang, P. J.; Zhdankin, V. V. Chem. Rev., in press. (b) Koser, G. F. In The Chemistry of Halides, Pseudo-Halides and Azides, Suppl. D2; Patai, S., Rappoport, Z., Eds.; Wiley-Interscience: Chichester, 1995; Chapter 21, pp 1173-1274. (c) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992.
    • (1992) The Organic Chemistry of Polycoordinated Iodine
    • Varvoglis, A.1
  • 58
    • 0004003407 scopus 로고
    • Elsevier: Amsterdam, The Netherlands
    • Brandsma, L. Preparative Acetylenic Chemistry; Elsevier: Amsterdam, The Netherlands, 1971. Williamson, B. L.; Stang, P. J.; Arif, A. M. J. Am. Chem. Soc. 1993, 115, 2590 and references therein.
    • (1971) Preparative Acetylenic Chemistry
    • Brandsma, L.1
  • 59
    • 0001394312 scopus 로고
    • and references therein
    • Brandsma, L. Preparative Acetylenic Chemistry; Elsevier: Amsterdam, The Netherlands, 1971. Williamson, B. L.; Stang, P. J.; Arif, A. M. J. Am. Chem. Soc. 1993, 115, 2590 and references therein.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 2590
    • Williamson, B.L.1    Stang, P.J.2    Arif, A.M.3


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