Cycloaddition-rearrangement sequence of 2-amido substituted furans as a method of synthesizing hexahydroindolinones

Journal of Organic Chemistry

Volumn 64, Issue 13, 1999, Pages 4617-4626

  Padwa, Albert ^a   Brodney, Michael A ^a   Satake, Kyosuke ^a   Straub, Christopher S ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 [2 (TERT BUTOXYCARBONYLFURAN 2 YL AMINO)ETHYL]ACRYLIC ACID METHYL ESTER; 3 CHLOROCARBONYLBUT 3 ENOIC ACID METHYL ESTER; ACRYLIC ACID METHYL ESTER; ALKENYL GROUP; HEXAHYDROINDOLINONE DERIVATIVE; INDOLE DERIVATIVE; OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033603620     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982061+     Document Type: Article

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51. For selected reviews, see: Lipshutz, B. H. Chem. Rev. 1986, 86, 795. Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173. Vogel, P. Bull. Soc. Chim. Belg. 1990, 99, 395. Lautens, M. Synlett 1993, 177. For leading references see: McGrath, D. V.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1991, 113, 3611. Bazan, G. C.; Oskam, J. H.; Cho, H. N.; Park, L. Y.; Schrock, R. R. J. Am. Chem. Soc. 1991, 113, 6899. Paquette, L. A.; Brown, D. S. J. Org. Chem. 1992, 57, 4512. Fattori, D.; Vogel, P. Tetrahedron Lett. 1993, 34, 1017. Lautens, M.; Chiu, P.; Colucci, J. T. Angew. Chem., Int. Ed. Engl. 1993, 32, 281. Ando, K.; Natano, C.; Akadegawa, N.; Shigihara, A.; Takayama, H. J. Chem. Soc., Chem. Commun. 1992, 870, Arai, Y.; Fujii, A.; Ohno, T.; Koizumi, T. Chem. Pharm. Bull. 1992, 40, 1670. Bloch, R.; Bortolussi, M.; Girard, C.; Seck, M. Tetrahedron 1992, 48, 453.
52. For selected reviews, see: Lipshutz, B. H. Chem. Rev. 1986, 86, 795. Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173. Vogel, P. Bull. Soc. Chim. Belg. 1990, 99, 395. Lautens, M. Synlett 1993, 177. For leading references see: McGrath, D. V.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1991, 113, 3611. Bazan, G. C.; Oskam, J. H.; Cho, H. N.; Park, L. Y.; Schrock, R. R. J. Am. Chem. Soc. 1991, 113, 6899. Paquette, L. A.; Brown, D. S. J. Org. Chem. 1992, 57, 4512. Fattori, D.; Vogel, P. Tetrahedron Lett. 1993, 34, 1017. Lautens, M.; Chiu, P.; Colucci, J. T. Angew. Chem., Int. Ed. Engl. 1993, 32, 281. Ando, K.; Natano, C.; Akadegawa, N.; Shigihara, A.; Takayama, H. J. Chem. Soc., Chem. Commun. 1992, 870, Arai, Y.; Fujii, A.; Ohno, T.; Koizumi, T. Chem. Pharm. Bull. 1992, 40, 1670. Bloch, R.; Bortolussi, M.; Girard, C.; Seck, M. Tetrahedron 1992, 48, 453.
53. For selected reviews, see: Lipshutz, B. H. Chem. Rev. 1986, 86, 795. Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173. Vogel, P. Bull. Soc. Chim. Belg. 1990, 99, 395. Lautens, M. Synlett 1993, 177. For leading references see: McGrath, D. V.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1991, 113, 3611. Bazan, G. C.; Oskam, J. H.; Cho, H. N.; Park, L. Y.; Schrock, R. R. J. Am. Chem. Soc. 1991, 113, 6899. Paquette, L. A.; Brown, D. S. J. Org. Chem. 1992, 57, 4512. Fattori, D.; Vogel, P. Tetrahedron Lett. 1993, 34, 1017. Lautens, M.; Chiu, P.; Colucci, J. T. Angew. Chem., Int. Ed. Engl. 1993, 32, 281. Ando, K.; Natano, C.; Akadegawa, N.; Shigihara, A.; Takayama, H. J. Chem. Soc., Chem. Commun. 1992, 870, Arai, Y.; Fujii, A.; Ohno, T.; Koizumi, T. Chem. Pharm. Bull. 1992, 40, 1670. Bloch, R.; Bortolussi, M.; Girard, C.; Seck, M. Tetrahedron 1992, 48, 453.
54. For selected reviews, see: Lipshutz, B. H. Chem. Rev. 1986, 86, 795. Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173. Vogel, P. Bull. Soc. Chim. Belg. 1990, 99, 395. Lautens, M. Synlett 1993, 177. For leading references see: McGrath, D. V.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1991, 113, 3611. Bazan, G. C.; Oskam, J. H.; Cho, H. N.; Park, L. Y.; Schrock, R. R. J. Am. Chem. Soc. 1991, 113, 6899. Paquette, L. A.; Brown, D. S. J. Org. Chem. 1992, 57, 4512. Fattori, D.; Vogel, P. Tetrahedron Lett. 1993, 34, 1017. Lautens, M.; Chiu, P.; Colucci, J. T. Angew. Chem., Int. Ed. Engl. 1993, 32, 281. Ando, K.; Natano, C.; Akadegawa, N.; Shigihara, A.; Takayama, H. J. Chem. Soc., Chem. Commun. 1992, 870, Arai, Y.; Fujii, A.; Ohno, T.; Koizumi, T. Chem. Pharm. Bull. 1992, 40, 1670. Bloch, R.; Bortolussi, M.; Girard, C.; Seck, M. Tetrahedron 1992, 48, 453.
55. For selected reviews, see: Lipshutz, B. H. Chem. Rev. 1986, 86, 795. Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173. Vogel, P. Bull. Soc. Chim. Belg. 1990, 99, 395. Lautens, M. Synlett 1993, 177. For leading references see: McGrath, D. V.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1991, 113, 3611. Bazan, G. C.; Oskam, J. H.; Cho, H. N.; Park, L. Y.; Schrock, R. R. J. Am. Chem. Soc. 1991, 113, 6899. Paquette, L. A.; Brown, D. S. J. Org. Chem. 1992, 57, 4512. Fattori, D.; Vogel, P. Tetrahedron Lett. 1993, 34, 1017. Lautens, M.; Chiu, P.; Colucci, J. T. Angew. Chem., Int. Ed. Engl. 1993, 32, 281. Ando, K.; Natano, C.; Akadegawa, N.; Shigihara, A.; Takayama, H. J. Chem. Soc., Chem. Commun. 1992, 870, Arai, Y.; Fujii, A.; Ohno, T.; Koizumi, T. Chem. Pharm. Bull. 1992, 40, 1670. Bloch, R.; Bortolussi, M.; Girard, C.; Seck, M. Tetrahedron 1992, 48, 453.
56. For selected reviews, see: Lipshutz, B. H. Chem. Rev. 1986, 86, 795. Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173. Vogel, P. Bull. Soc. Chim. Belg. 1990, 99, 395. Lautens, M. Synlett 1993, 177. For leading references see: McGrath, D. V.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1991, 113, 3611. Bazan, G. C.; Oskam, J. H.; Cho, H. N.; Park, L. Y.; Schrock, R. R. J. Am. Chem. Soc. 1991, 113, 6899. Paquette, L. A.; Brown, D. S. J. Org. Chem. 1992, 57, 4512. Fattori, D.; Vogel, P. Tetrahedron Lett. 1993, 34, 1017. Lautens, M.; Chiu, P.; Colucci, J. T. Angew. Chem., Int. Ed. Engl. 1993, 32, 281. Ando, K.; Natano, C.; Akadegawa, N.; Shigihara, A.; Takayama, H. J. Chem. Soc., Chem. Commun. 1992, 870, Arai, Y.; Fujii, A.; Ohno, T.; Koizumi, T. Chem. Pharm. Bull. 1992, 40, 1670. Bloch, R.; Bortolussi, M.; Girard, C.; Seck, M. Tetrahedron 1992, 48, 453.
57. For selected reviews, see: Lipshutz, B. H. Chem. Rev. 1986, 86, 795. Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173. Vogel, P. Bull. Soc. Chim. Belg. 1990, 99, 395. Lautens, M. Synlett 1993, 177. For leading references see: McGrath, D. V.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1991, 113, 3611. Bazan, G. C.; Oskam, J. H.; Cho, H. N.; Park, L. Y.; Schrock, R. R. J. Am. Chem. Soc. 1991, 113, 6899. Paquette, L. A.; Brown, D. S. J. Org. Chem. 1992, 57, 4512. Fattori, D.; Vogel, P. Tetrahedron Lett. 1993, 34, 1017. Lautens, M.; Chiu, P.; Colucci, J. T. Angew. Chem., Int. Ed. Engl. 1993, 32, 281. Ando, K.; Natano, C.; Akadegawa, N.; Shigihara, A.; Takayama, H. J. Chem. Soc., Chem. Commun. 1992, 870, Arai, Y.; Fujii, A.; Ohno, T.; Koizumi, T. Chem. Pharm. Bull. 1992, 40, 1670. Bloch, R.; Bortolussi, M.; Girard, C.; Seck, M. Tetrahedron 1992, 48, 453.
58. For selected reviews, see: Lipshutz, B. H. Chem. Rev. 1986, 86, 795. Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173. Vogel, P. Bull. Soc. Chim. Belg. 1990, 99, 395. Lautens, M. Synlett 1993, 177. For leading references see: McGrath, D. V.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1991, 113, 3611. Bazan, G. C.; Oskam, J. H.; Cho, H. N.; Park, L. Y.; Schrock, R. R. J. Am. Chem. Soc. 1991, 113, 6899. Paquette, L. A.; Brown, D. S. J. Org. Chem. 1992, 57, 4512. Fattori, D.; Vogel, P. Tetrahedron Lett. 1993, 34, 1017. Lautens, M.; Chiu, P.; Colucci, J. T. Angew. Chem., Int. Ed. Engl. 1993, 32, 281. Ando, K.; Natano, C.; Akadegawa, N.; Shigihara, A.; Takayama, H. J. Chem. Soc., Chem. Commun. 1992, 870, Arai, Y.; Fujii, A.; Ohno, T.; Koizumi, T. Chem. Pharm. Bull. 1992, 40, 1670. Bloch, R.; Bortolussi, M.; Girard, C.; Seck, M. Tetrahedron 1992, 48, 453.
59. For selected reviews, see: Lipshutz, B. H. Chem. Rev. 1986, 86, 795. Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173. Vogel, P. Bull. Soc. Chim. Belg. 1990, 99, 395. Lautens, M. Synlett 1993, 177. For leading references see: McGrath, D. V.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1991, 113, 3611. Bazan, G. C.; Oskam, J. H.; Cho, H. N.; Park, L. Y.; Schrock, R. R. J. Am. Chem. Soc. 1991, 113, 6899. Paquette, L. A.; Brown, D. S. J. Org. Chem. 1992, 57, 4512. Fattori, D.; Vogel, P. Tetrahedron Lett. 1993, 34, 1017. Lautens, M.; Chiu, P.; Colucci, J. T. Angew. Chem., Int. Ed. Engl. 1993, 32, 281. Ando, K.; Natano, C.; Akadegawa, N.; Shigihara, A.; Takayama, H. J. Chem. Soc., Chem. Commun. 1992, 870, Arai, Y.; Fujii, A.; Ohno, T.; Koizumi, T. Chem. Pharm. Bull. 1992, 40, 1670. Bloch, R.; Bortolussi, M.; Girard, C.; Seck, M. Tetrahedron 1992, 48, 453.
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