메뉴 건너뛰기




Volumn 38, Issue 36, 1997, Pages 6313-6316

Radical induced cyclopropane fragmentation - H-abstraction - Cyclization cascade: Synthesis of carbocyclic systems containing bridgehead methyl groups

Author keywords

[No Author keywords available]

Indexed keywords

INDAN DERIVATIVE; ISOBENZOFURAN DERIVATIVE;

EID: 0030864044     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01450-0     Document Type: Article
Times cited : (9)

References (42)
  • 1
    • 85082777144 scopus 로고
    • General reviews on radical chemistry: (a) Curran, D. P. Synthesis 1988, 417-439 and 489-512. (b) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 715-777 and pp 779-899. (c) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Organic Reactions, 1996, 48, 301-856.
    • (1988) Synthesis , pp. 417-439
    • Curran, D.P.1
  • 2
    • 0001216647 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
    • General reviews on radical chemistry: (a) Curran, D. P. Synthesis 1988, 417-439 and 489-512. (b) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 715-777 and pp 779-899. (c) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Organic Reactions, 1996, 48, 301-856.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 715-777
    • Curran, D.P.1
  • 3
    • 0000893313 scopus 로고    scopus 로고
    • General reviews on radical chemistry: (a) Curran, D. P. Synthesis 1988, 417-439 and 489-512. (b) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 715-777 and pp 779-899. (c) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Organic Reactions, 1996, 48, 301-856.
    • (1996) Organic Reactions , vol.48 , pp. 301-856
    • Giese, B.1    Kopping, B.2    Göbel, T.3    Dickhaut, J.4    Thoma, G.5    Kulicke, K.J.6    Trach, F.7
  • 4
    • 0000702878 scopus 로고
    • Radical reactions in natural product synthesis
    • Tandem radical reactions: (a) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. "Radical reactions in natural product synthesis," Chem. Rev. 1991, 91, 1237-1286. (b) Curran, D. P. In Adv. Free Radical Chem.; Tanner, D. D., Ed.; Jai Press, Inc.: Greenwich, CT, 1990; Vol. 1, pp. 121-157 (c) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (d) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195-206. (e) Malacria, M. Chem. Rev. 1996, 96, 289-306.
    • (1991) Chem. Rev. , vol.91 , pp. 1237-1286
    • Jasperse, C.P.1    Curran, D.P.2    Fevig, T.L.3
  • 5
    • 0000702878 scopus 로고
    • Tanner, D. D., Ed.; Jai Press, Inc.: Greenwich, CT
    • Tandem radical reactions: (a) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. "Radical reactions in natural product synthesis," Chem. Rev. 1991, 91, 1237-1286. (b) Curran, D. P. In Adv. Free Radical Chem.; Tanner, D. D., Ed.; Jai Press, Inc.: Greenwich, CT, 1990; Vol. 1, pp. 121-157 (c) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (d) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195-206. (e) Malacria, M. Chem. Rev. 1996, 96, 289-306.
    • (1990) Adv. Free Radical Chem. , vol.1 , pp. 121-157
    • Curran, D.P.1
  • 6
    • 0028879573 scopus 로고
    • Tandem radical reactions: (a) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. "Radical reactions in natural product synthesis," Chem. Rev. 1991, 91, 1237-1286. (b) Curran, D. P. In Adv. Free Radical Chem.; Tanner, D. D., Ed.; Jai Press, Inc.: Greenwich, CT, 1990; Vol. 1, pp. 121-157 (c) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (d) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195-206. (e) Malacria, M. Chem. Rev. 1996, 96, 289-306.
    • (1995) Tetrahedron , vol.51 , pp. 13103-13159
    • Bunce, R.A.1
  • 7
    • 0001146788 scopus 로고    scopus 로고
    • Tandem radical reactions: (a) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. "Radical reactions in natural product synthesis," Chem. Rev. 1991, 91, 1237-1286. (b) Curran, D. P. In Adv. Free Radical Chem.; Tanner, D. D., Ed.; Jai Press, Inc.: Greenwich, CT, 1990; Vol. 1, pp. 121-157 (c) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (d) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195-206. (e) Malacria, M. Chem. Rev. 1996, 96, 289-306.
    • (1996) Chem. Rev. , vol.96 , pp. 195-206
    • Parsons, P.J.1    Penkett, C.S.2    Shell, A.J.3
  • 8
    • 0000721036 scopus 로고    scopus 로고
    • Tandem radical reactions: (a) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. "Radical reactions in natural product synthesis," Chem. Rev. 1991, 91, 1237-1286. (b) Curran, D. P. In Adv. Free Radical Chem.; Tanner, D. D., Ed.; Jai Press, Inc.: Greenwich, CT, 1990; Vol. 1, pp. 121-157 (c) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. (d) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195-206. (e) Malacria, M. Chem. Rev. 1996, 96, 289-306.
    • (1996) Chem. Rev. , vol.96 , pp. 289-306
    • Malacria, M.1
  • 22
    • 0000030495 scopus 로고
    • and references cited therein
    • (b) Curran, D. P.; Shen, W. J. Am. Chem. Soc. 1993, 115, 6051-6059 and references cited therein,
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 6051-6059
    • Curran, D.P.1    Shen, W.2
  • 25
    • 0025265145 scopus 로고
    • For selected examples, see: (a) Boivin, J.; da Silva, E.; Ourisson, G.; Zard, S. Z. Tetrahedron Lett. 1990, 31, 2501-2504. (b) Boivin, J.; Fouquet, E.; Zard, S. Z. J. Am. Chem. Soc. 1991, 113, 1055-1057. (c) Brunckova, J.; Crich, D.; Yao, Q. Tetrahedron Lett. 1994, 35, 6619-6622. (d) Masnyk, M. Tetrahedron Lett. 1997, 38, 879- 882. Theoretical Studies: (e) Huang, X. L.; Dannenberg, J. J. J. Org. Chem. 1991, 56, 5421-5424. (f) Viskolcz, B.; Lendvay, G.; Kortvelyesi, T.; Seres, L. J. Am. Chem. Soc. 1996, 118, 3006-3009.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 2501-2504
    • Boivin, J.1    Da Silva, E.2    Ourisson, G.3    Zard, S.Z.4
  • 26
    • 0000424304 scopus 로고
    • For selected examples, see: (a) Boivin, J.; da Silva, E.; Ourisson, G.; Zard, S. Z. Tetrahedron Lett. 1990, 31, 2501-2504. (b) Boivin, J.; Fouquet, E.; Zard, S. Z. J. Am. Chem. Soc. 1991, 113, 1055-1057. (c) Brunckova, J.; Crich, D.; Yao, Q. Tetrahedron Lett. 1994, 35, 6619-6622. (d) Masnyk, M. Tetrahedron Lett. 1997, 38, 879- 882. Theoretical Studies: (e) Huang, X. L.; Dannenberg, J. J. J. Org. Chem. 1991, 56, 5421-5424. (f) Viskolcz, B.; Lendvay, G.; Kortvelyesi, T.; Seres, L. J. Am. Chem. Soc. 1996, 118, 3006-3009.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 1055-1057
    • Boivin, J.1    Fouquet, E.2    Zard, S.Z.3
  • 27
    • 0028122946 scopus 로고
    • For selected examples, see: (a) Boivin, J.; da Silva, E.; Ourisson, G.; Zard, S. Z. Tetrahedron Lett. 1990, 31, 2501-2504. (b) Boivin, J.; Fouquet, E.; Zard, S. Z. J. Am. Chem. Soc. 1991, 113, 1055-1057. (c) Brunckova, J.; Crich, D.; Yao, Q. Tetrahedron Lett. 1994, 35, 6619-6622. (d) Masnyk, M. Tetrahedron Lett. 1997, 38, 879- 882. Theoretical Studies: (e) Huang, X. L.; Dannenberg, J. J. J. Org. Chem. 1991, 56, 5421-5424. (f) Viskolcz, B.; Lendvay, G.; Kortvelyesi, T.; Seres, L. J. Am. Chem. Soc. 1996, 118, 3006-3009.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 6619-6622
    • Brunckova, J.1    Crich, D.2    Yao, Q.3
  • 28
    • 0031033167 scopus 로고    scopus 로고
    • For selected examples, see: (a) Boivin, J.; da Silva, E.; Ourisson, G.; Zard, S. Z. Tetrahedron Lett. 1990, 31, 2501-2504. (b) Boivin, J.; Fouquet, E.; Zard, S. Z. J. Am. Chem. Soc. 1991, 113, 1055-1057. (c) Brunckova, J.; Crich, D.; Yao, Q. Tetrahedron Lett. 1994, 35, 6619-6622. (d) Masnyk, M. Tetrahedron Lett. 1997, 38, 879-882. Theoretical Studies: (e) Huang, X. L.; Dannenberg, J. J. J. Org. Chem. 1991, 56, 5421-5424. (f) Viskolcz, B.; Lendvay, G.; Kortvelyesi, T.; Seres, L. J. Am. Chem. Soc. 1996, 118, 3006-3009.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 879-882
    • Masnyk, M.1
  • 29
    • 0000670439 scopus 로고
    • For selected examples, see: (a) Boivin, J.; da Silva, E.; Ourisson, G.; Zard, S. Z. Tetrahedron Lett. 1990, 31, 2501-2504. (b) Boivin, J.; Fouquet, E.; Zard, S. Z. J. Am. Chem. Soc. 1991, 113, 1055-1057. (c) Brunckova, J.; Crich, D.; Yao, Q. Tetrahedron Lett. 1994, 35, 6619-6622. (d) Masnyk, M. Tetrahedron Lett. 1997, 38, 879- 882. Theoretical Studies: (e) Huang, X. L.; Dannenberg, J. J. J. Org. Chem. 1991, 56, 5421-5424. (f) Viskolcz, B.; Lendvay, G.; Kortvelyesi, T.; Seres, L. J. Am. Chem. Soc. 1996, 118, 3006-3009.
    • (1991) J. Org. Chem. , vol.56 , pp. 5421-5424
    • Huang, X.L.1    Dannenberg, J.J.2
  • 30
    • 85032384311 scopus 로고    scopus 로고
    • For selected examples, see: (a) Boivin, J.; da Silva, E.; Ourisson, G.; Zard, S. Z. Tetrahedron Lett. 1990, 31, 2501-2504. (b) Boivin, J.; Fouquet, E.; Zard, S. Z. J. Am. Chem. Soc. 1991, 113, 1055-1057. (c) Brunckova, J.; Crich, D.; Yao, Q. Tetrahedron Lett. 1994, 35, 6619-6622. (d) Masnyk, M. Tetrahedron Lett. 1997, 38, 879- 882. Theoretical Studies: (e) Huang, X. L.; Dannenberg, J. J. J. Org. Chem. 1991, 56, 5421-5424. (f) Viskolcz, B.; Lendvay, G.; Kortvelyesi, T.; Seres, L. J. Am. Chem. Soc. 1996, 118, 3006-3009.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 3006-3009
    • Viskolcz, B.1    Lendvay, G.2    Kortvelyesi, T.3    Seres, L.4
  • 35
    • 0343804964 scopus 로고    scopus 로고
    • note
    • 3, 62.9 MHz) δ (multiplicity) 11: 208.9 (s), 138.4 (s), 128.3 (d), 127.6 (d), 127.5 (d), 72.9 (t), 69.9 (t), 36.1 (t), 35.5 (t), 33.6 (d), 27.8 (s), 26.6 (t), 25.5 (t), 18.3 (t), 17.1 (t); 12: 213.6 (s), 213.2 (s), 138.5 (s), 128.3 (d), 128.2 (d), 127.5 (d), 127.4 (d), 127.3 (d), 127.2 (d), 84.3 (d), 82.3 (d), 71.3 (t), 71.0 (t), 66.8 (d), 64.5 (d), 46.6 (s), 43.6 (s), 41.8 (t), 39.8 (t), 39.2 (t), 37.8 (t), 34.9 (t), 34.4 (t), 30.9 (t), 30.8 (t), 27.9 (q), 27.2 (q), 22.2 (t), 21.1 (t).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.