A facile preparation of exo-Cyclic conjugated dienes fused to lactams or lactones via intramolecular coupling of acetylenes and their behavior in Diels-Alder reactions

Organic Letters

Volumn 2, Issue 22, 2000, Pages 3481-3484

  Urabe, Hirokazu ^a   Nakajima, Ryota ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; ALKENE; DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; LACTAM; LACTONE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ACETYLENE; ALKENES; INDICATORS AND REAGENTS; LACTAMS; LACTONES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0034597506     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0065221     Document Type: Article

References (43)

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11. For review on group 4 metal-mediated diyne cyclization, see: Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058. Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 1163-1184. Broene, R. D.; Buchwald, S. L. Science 1993, 261, 1696-1701. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124-130. Maier, M. In Organic Synthesis Highlights II; Waldmann, H., Ed.; VCH: Weinheim, 1995; pp 99-113. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arndt, P.; Burlakov, V. V.; Rosenthal, U. Synlett 1996, 111-118. Negishi, E.; Takahashi, T. Bull. Chem. Soc. Jpn. 1998, 71, 755-769.
12. For review on group 4 metal-mediated diyne cyclization, see: Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058. Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 1163-1184. Broene, R. D.; Buchwald, S. L. Science 1993, 261, 1696-1701. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124-130. Maier, M. In Organic Synthesis Highlights II; Waldmann, H., Ed.; VCH: Weinheim, 1995; pp 99-113. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arndt, P.; Burlakov, V. V.; Rosenthal, U. Synlett 1996, 111-118. Negishi, E.; Takahashi, T. Bull. Chem. Soc. Jpn. 1998, 71, 755-769.
13. For review on group 4 metal-mediated diyne cyclization, see: Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058. Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 1163-1184. Broene, R. D.; Buchwald, S. L. Science 1993, 261, 1696-1701. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124-130. Maier, M. In Organic Synthesis Highlights II; Waldmann, H., Ed.; VCH: Weinheim, 1995; pp 99-113. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arndt, P.; Burlakov, V. V.; Rosenthal, U. Synlett 1996, 111-118. Negishi, E.; Takahashi, T. Bull. Chem. Soc. Jpn. 1998, 71, 755-769.
14. For review on group 4 metal-mediated diyne cyclization, see: Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058. Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 1163-1184. Broene, R. D.; Buchwald, S. L. Science 1993, 261, 1696-1701. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124-130. Maier, M. In Organic Synthesis Highlights II; Waldmann, H., Ed.; VCH: Weinheim, 1995; pp 99-113. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arndt, P.; Burlakov, V. V.; Rosenthal, U. Synlett 1996, 111-118. Negishi, E.; Takahashi, T. Bull. Chem. Soc. Jpn. 1998, 71, 755-769.
15. For the preparation of dienes via diyne cyclization mediated by transition metals other than group 4, see: Trost, B. M.; Krische, M. J. Synlett 1998, 1-16. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281. Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539-546. Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42.
16. For the preparation of dienes via diyne cyclization mediated by transition metals other than group 4, see: Trost, B. M.; Krische, M. J. Synlett 1998, 1-16. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281. Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539-546. Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42.
17. For the preparation of dienes via diyne cyclization mediated by transition metals other than group 4, see: Trost, B. M.; Krische, M. J. Synlett 1998, 1-16. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281. Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539-546. Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42.
18. For the preparation of dienes via diyne cyclization mediated by transition metals other than group 4, see: Trost, B. M.; Krische, M. J. Synlett 1998, 1-16. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281. Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539-546. Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42.
19. For the preparation of dienes via diyne cyclization mediated by transition metals other than group 4, see: Trost, B. M.; Krische, M. J. Synlett 1998, 1-16. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281. Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539-546. Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42.
20. For the preparation of dienes via diyne cyclization mediated by transition metals other than group 4, see: Trost, B. M.; Krische, M. J. Synlett 1998, 1-16. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281. Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539-546. Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42.
21. A preparation of polycyclic compounds based on the cyclization of diyne 1 with a group 4 metalocene reagent followed by Diels-Alder reaction was reported; see: Nugent, W. A.; Calabrese, J. C. J. Am. Chem. Soc. 1984, 106, 6422-6424.
22. Formation of functionalized rhodacycles similar to 7 in Scheme 1 is known, but its conversion to diene upon hydrolysis is not clear. Müller, E. Synthesis 1974, 761-774.
23. Some attempts to promote the cyclization of similar functionalized enynes were unsuccessful. An enyne tethered by an ester analogous to 14 in Table 1 failed in the titanocene-mediated cyclization. Zhao, Z.; Ding, Y.; Zhao, G. J. Org. Chem. 1998, 63, 9285-9291. Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593-8601. Palladium-catalyzed arylative cyclization of an enyne tethered by amide afforded a product similar to 17 only in a low yield. Xie, X.; Lu, X. Tetrahedron Lett. 1999, 40, 8415-8418. See also: Lu, X.; Zhu, G.; Wang, Z. Synlett 1998, 115-121.
24. Some attempts to promote the cyclization of similar functionalized enynes were unsuccessful. An enyne tethered by an ester analogous to 14 in Table 1 failed in the titanocene-mediated cyclization. Zhao, Z.; Ding, Y.; Zhao, G. J. Org. Chem. 1998, 63, 9285-9291. Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593-8601. Palladium-catalyzed arylative cyclization of an enyne tethered by amide afforded a product similar to 17 only in a low yield. Xie, X.; Lu, X. Tetrahedron Lett. 1999, 40, 8415-8418. See also: Lu, X.; Zhu, G.; Wang, Z. Synlett 1998, 115-121.
25. Some attempts to promote the cyclization of similar functionalized enynes were unsuccessful. An enyne tethered by an ester analogous to 14 in Table 1 failed in the titanocene-mediated cyclization. Zhao, Z.; Ding, Y.; Zhao, G. J. Org. Chem. 1998, 63, 9285-9291. Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593-8601. Palladium-catalyzed arylative cyclization of an enyne tethered by amide afforded a product similar to 17 only in a low yield. Xie, X.; Lu, X. Tetrahedron Lett. 1999, 40, 8415-8418. See also: Lu, X.; Zhu, G.; Wang, Z. Synlett 1998, 115-121.
26. Some attempts to promote the cyclization of similar functionalized enynes were unsuccessful. An enyne tethered by an ester analogous to 14 in Table 1 failed in the titanocene-mediated cyclization. Zhao, Z.; Ding, Y.; Zhao, G. J. Org. Chem. 1998, 63, 9285-9291. Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593-8601. Palladium-catalyzed arylative cyclization of an enyne tethered by amide afforded a product similar to 17 only in a low yield. Xie, X.; Lu, X. Tetrahedron Lett. 1999, 40, 8415-8418. See also: Lu, X.; Zhu, G.; Wang, Z. Synlett 1998, 115-121.
27. Hamada, T.; Suzuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 1999, 121, 7342-7344.
28. Sato, F.; Urabe, H.; Okamoto, S. Pure Appl. Chem. 1999, 71, 1511-1519. Sato, F.; Urabe, H.; Okamoto, S. Synlett 2000, 753-775. Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835-2886.
29. Sato, F.; Urabe, H.; Okamoto, S. Pure Appl. Chem. 1999, 71, 1511-1519. Sato, F.; Urabe, H.; Okamoto, S. Synlett 2000, 753-775. Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835-2886.
30. Sato, F.; Urabe, H.; Okamoto, S. Pure Appl. Chem. 1999, 71, 1511-1519. Sato, F.; Urabe, H.; Okamoto, S. Synlett 2000, 753-775. Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835-2886.
31. In an intermolecular cyclization where no positional bias exists, a nonsilylated propiolic amide 29 was incorporated into the diene 30 exclusively with its amide group being placed at the terminal position of the diene system, which is not the case in 16 of entry 2, Table 1. (Equation Presented)
32. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976; pp 132-136.
33. Juaristi, E.; León-Romo, J. L.; Reyes, A.; Escalante, J. Tetrahedron: Asymmetry 1999, 10, 2441-2495. Bloch, R. Chem. Rev. 1998, 98, 1407-1438. Enders, D.; Reinhold: U. Tetrahedron: Asymmetry 1997, 8, 1895-1946.
34. Juaristi, E.; León-Romo, J. L.; Reyes, A.; Escalante, J. Tetrahedron: Asymmetry 1999, 10, 2441-2495. Bloch, R. Chem. Rev. 1998, 98, 1407-1438. Enders, D.; Reinhold: U. Tetrahedron: Asymmetry 1997, 8, 1895-1946.
35. Juaristi, E.; León-Romo, J. L.; Reyes, A.; Escalante, J. Tetrahedron: Asymmetry 1999, 10, 2441-2495. Bloch, R. Chem. Rev. 1998, 98, 1407-1438. Enders, D.; Reinhold: U. Tetrahedron: Asymmetry 1997, 8, 1895-1946.
36. 4, and concentrated in vacuo to give a crude oil, which was chromatographed on silica gel (hexanes-ether) to afford the title compound (32 mg. 80%) as an oil.
37. The nitrogen heterocycles obtained herein will be useful intermediates for the synthesis of both pyrrolidine and isoindoline derivatives. Cordell, G. A., Saxton, J. E., Shamma, M., Smith, G. F., Eds. Dictionary of Alkaloids; Chapman and Hall: London, 1989. Glasby, J. S., Ed. Encyclopedia of the Alkaloids; Plenum Press: New York, 1975.
38. The nitrogen heterocycles obtained herein will be useful intermediates for the synthesis of both pyrrolidine and isoindoline derivatives. Cordell, G. A., Saxton, J. E., Shamma, M., Smith, G. F., Eds. Dictionary of Alkaloids; Chapman and Hall: London, 1989. Glasby, J. S., Ed. Encyclopedia of the Alkaloids; Plenum Press: New York, 1975.
39. For further elaboration based on the silylated diene and allylsilane moieties in the products, see: Luh, T.-Y.; Wong, K.-T. Synthesis 1993, 349-370. Weber, W. P. In Silicon Reagents for Organic Synthesis; Spnnger-Verlag: Berlin, 1983. Colvin, E. W. In Silicon in Organic Synthesis; Butterworth: London, 1981. Fleming, I.; Dunogués, J.; Smithers, R. In Organic Reactions; Kende, A. S., Ed.; Wiley: New York, 1989; Vol. 37, pp 57-575. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063-2192.
40. For further elaboration based on the silylated diene and allylsilane moieties in the products, see: Luh, T.-Y.; Wong, K.-T. Synthesis 1993, 349-370. Weber, W. P. In Silicon Reagents for Organic Synthesis; Spnnger-Verlag: Berlin, 1983. Colvin, E. W. In Silicon in Organic Synthesis; Butterworth: London, 1981. Fleming, I.; Dunogués, J.; Smithers, R. In Organic Reactions; Kende, A. S., Ed.; Wiley: New York, 1989; Vol. 37, pp 57-575. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063-2192.
41. For further elaboration based on the silylated diene and allylsilane moieties in the products, see: Luh, T.-Y.; Wong, K.-T. Synthesis 1993, 349-370. Weber, W. P. In Silicon Reagents for Organic Synthesis; Spnnger-Verlag: Berlin, 1983. Colvin, E. W. In Silicon in Organic Synthesis; Butterworth: London, 1981. Fleming, I.; Dunogués, J.; Smithers, R. In Organic Reactions; Kende, A. S., Ed.; Wiley: New York, 1989; Vol. 37, pp 57-575. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063-2192.
42. For further elaboration based on the silylated diene and allylsilane moieties in the products, see: Luh, T.-Y.; Wong, K.-T. Synthesis 1993, 349-370. Weber, W. P. In Silicon Reagents for Organic Synthesis; Spnnger-Verlag: Berlin, 1983. Colvin, E. W. In Silicon in Organic Synthesis; Butterworth: London, 1981. Fleming, I.; Dunogués, J.; Smithers, R. In Organic Reactions; Kende, A. S., Ed.; Wiley: New York, 1989; Vol. 37, pp 57-575. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063-2192.
43. For further elaboration based on the silylated diene and allylsilane moieties in the products, see: Luh, T.-Y.; Wong, K.-T. Synthesis 1993, 349-370. Weber, W. P. In Silicon Reagents for Organic Synthesis; Spnnger-Verlag: Berlin, 1983. Colvin, E. W. In Silicon in Organic Synthesis; Butterworth: London, 1981. Fleming, I.; Dunogués, J.; Smithers, R. In Organic Reactions; Kende, A. S., Ed.; Wiley: New York, 1989; Vol. 37, pp 57-575. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063-2192.