메뉴 건너뛰기




Volumn 14, Issue 19, 2003, Pages 3033-3041

Synthesis of (-)-aphanorphine using a sulfur-directed aryl radical cyclization

Author keywords

[No Author keywords available]

Indexed keywords

1 BENZYLOXYCARBONYL 2 (2 BROMO 4 METHOXYPHENYL)METHYL 2 METHOXYCARBONYL 4 (PHENYLTHIOMETHYLENE)PYRROLIDINE; 1 BENZYLOXYCARBONYL 2 [(2 BROMOPHENYL)METHYL] 2 METHOXYCARBONYL 4 (METHYLENE)PYRROLIDINE; 1 BENZYLOXYCARBONYL 2 [(2 BROMOPHENYL)METHYL] 2 METHOXYCARBONYL 4 (PHENYLTHIOMETHYLENE)PYRROLIDINE; 1 BENZYLOXYCARBONYL 2 BENZYL 2 METHOXYCARBONYL 4 METHYL 3 PYRROLINE; 3 BENZYLOXYCARBONYL 4 METHOXYCARBONYL 1 (PHENYLTHIO)METHYL 2,3,4,5 TETRAHYDRO 1,4 METHANO 3 BENZAZEPINE; 3 BENZYLOXYCARBONYL 4 METHOXYCARBONYL 1 METHYL 2,3,4,5 TETRAHYDRO 1,4 METHANO 3 BENZAZEPINE; ALKALOID DERIVATIVE; ALKENE DERIVATIVE; APHANORPHINE; BENZENE DERIVATIVE; CARBENOID; HYDROGEN; SULFUR; UNCLASSIFIED DRUG;

EID: 1842473650     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00530-5     Document Type: Article
Times cited : (40)

References (29)
  • 3
    • 0025365543 scopus 로고
    • For synthesis of (-)-1, see: (a) Takano, S.; Inomata, K.; Sato, T.; Takahashi, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1990, 290; (b) Shimizu, M.; Kamikubo, T.; Ogasawara, K. Heterocycles 1997, 46, 21; (c) Meyers, A. I.; Schmidt, W.; Santiago, B. Heterocycles 1995, 40, 525; (d) Shiotani, S.; Okada, H.; Nakamata, K.; Yamamoto, T.; Sekino, F. Heterocycles 1996, 43, 1031.
    • (1990) J. Chem. Soc., Chem. Commun. , pp. 290
    • Takano, S.1    Inomata, K.2    Sato, T.3    Takahashi, M.4    Ogasawara, K.5
  • 4
    • 0011882244 scopus 로고    scopus 로고
    • For synthesis of (-)-1, see: (a) Takano, S.; Inomata, K.; Sato, T.; Takahashi, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1990, 290; (b) Shimizu, M.; Kamikubo, T.; Ogasawara, K. Heterocycles 1997, 46, 21; (c) Meyers, A. I.; Schmidt, W.; Santiago, B. Heterocycles 1995, 40, 525; (d) Shiotani, S.; Okada, H.; Nakamata, K.; Yamamoto, T.; Sekino, F. Heterocycles 1996, 43, 1031.
    • (1997) , vol.46 , pp. 21
    • Shimizu, M.1    Kamikubo, T.2    Heterocycles, O.K.3
  • 5
    • 0000634625 scopus 로고
    • For synthesis of (-)-1, see: (a) Takano, S.; Inomata, K.; Sato, T.; Takahashi, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1990, 290; (b) Shimizu, M.; Kamikubo, T.; Ogasawara, K. Heterocycles 1997, 46, 21; (c) Meyers, A. I.; Schmidt, W.; Santiago, B. Heterocycles 1995, 40, 525; (d) Shiotani, S.; Okada, H.; Nakamata, K.; Yamamoto, T.; Sekino, F. Heterocycles 1996, 43, 1031.
    • (1995) Heterocycles , vol.40 , pp. 525
    • Meyers, A.I.1    Schmidt, W.2    Santiago, B.3
  • 6
    • 0000118162 scopus 로고    scopus 로고
    • For synthesis of (-)-1, see: (a) Takano, S.; Inomata, K.; Sato, T.; Takahashi, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1990, 290; (b) Shimizu, M.; Kamikubo, T.; Ogasawara, K. Heterocycles 1997, 46, 21; (c) Meyers, A. I.; Schmidt, W.; Santiago, B. Heterocycles 1995, 40, 525; (d) Shiotani, S.; Okada, H.; Nakamata, K.; Yamamoto, T.; Sekino, F. Heterocycles 1996, 43, 1031.
    • (1996) Heterocycles , vol.43 , pp. 1031
    • Shiotani, S.1    Okada, H.2    Nakamata, K.3    Yamamoto, T.4    Sekino, F.5
  • 8
    • 0028899294 scopus 로고
    • For syntheses of intermediates and related compounds, see: (a) Hulme, A. N.; Henry, S. S.; Meyers, A. I. J. Org. Chem. 1995, 60, 1265; (b) Fadel, A.; Arzel, P. Tetrahedron: Asymmetry 1995, 6, 893; (c) Hallinan, K. O.; Honda, T. Tetrahedron 1995, 51, 12211; (d) Node, M.; Imazato, H.; Kurosaki, R.; Kawano, Y.; Inoue, T.; Nishide, K.; Fuji, K. Heterocycles 1996, 42, 811; (e) Fadel, A.; Arzel, P. Tetrahedron: Asymmetry 1997, 8, 371.
    • (1995) J. Org. Chem. , vol.60 , pp. 1265
    • Hulme, A.N.1    Henry, S.S.2    Meyers, A.I.3
  • 9
    • 0028913332 scopus 로고
    • For syntheses of intermediates and related compounds, see: (a) Hulme, A. N.; Henry, S. S.; Meyers, A. I. J. Org. Chem. 1995, 60, 1265; (b) Fadel, A.; Arzel, P. Tetrahedron: Asymmetry 1995, 6, 893; (c) Hallinan, K. O.; Honda, T. Tetrahedron 1995, 51, 12211; (d) Node, M.; Imazato, H.; Kurosaki, R.; Kawano, Y.; Inoue, T.; Nishide, K.; Fuji, K. Heterocycles 1996, 42, 811; (e) Fadel, A.; Arzel, P. Tetrahedron: Asymmetry 1997, 8, 371.
    • (1995) Tetrahedron: Asymmetry , vol.6 , pp. 893
    • Fadel, A.1    Arzel, P.2
  • 10
    • 0028858096 scopus 로고
    • For syntheses of intermediates and related compounds, see: (a) Hulme, A. N.; Henry, S. S.; Meyers, A. I. J. Org. Chem. 1995, 60, 1265; (b) Fadel, A.; Arzel, P. Tetrahedron: Asymmetry 1995, 6, 893; (c) Hallinan, K. O.; Honda, T. Tetrahedron 1995, 51, 12211; (d) Node, M.; Imazato, H.; Kurosaki, R.; Kawano, Y.; Inoue, T.; Nishide, K.; Fuji, K. Heterocycles 1996, 42, 811; (e) Fadel, A.; Arzel, P. Tetrahedron: Asymmetry 1997, 8, 371.
    • (1995) Tetrahedron , vol.51 , pp. 12211
    • Hallinan, K.O.1    Honda, T.2
  • 11
    • 0007906819 scopus 로고    scopus 로고
    • For syntheses of intermediates and related compounds, see: (a) Hulme, A. N.; Henry, S. S.; Meyers, A. I. J. Org. Chem. 1995, 60, 1265; (b) Fadel, A.; Arzel, P. Tetrahedron: Asymmetry 1995, 6, 893; (c) Hallinan, K. O.; Honda, T. Tetrahedron 1995, 51, 12211; (d) Node, M.; Imazato, H.; Kurosaki, R.; Kawano, Y.; Inoue, T.; Nishide, K.; Fuji, K. Heterocycles 1996, 42, 811; (e) Fadel, A.; Arzel, P. Tetrahedron: Asymmetry 1997, 8, 371.
    • (1996) Heterocycles , vol.42 , pp. 811
    • Node, M.1    Imazato, H.2    Kurosaki, R.3    Kawano, Y.4    Inoue, T.5    Nishide, K.6    Fuji, K.7
  • 12
    • 0031046483 scopus 로고    scopus 로고
    • For syntheses of intermediates and related compounds, see: (a) Hulme, A. N.; Henry, S. S.; Meyers, A. I. J. Org. Chem. 1995, 60, 1265; (b) Fadel, A.; Arzel, P. Tetrahedron: Asymmetry 1995, 6, 893; (c) Hallinan, K. O.; Honda, T. Tetrahedron 1995, 51, 12211; (d) Node, M.; Imazato, H.; Kurosaki, R.; Kawano, Y.; Inoue, T.; Nishide, K.; Fuji, K. Heterocycles 1996, 42, 811; (e) Fadel, A.; Arzel, P. Tetrahedron: Asymmetry 1997, 8, 371.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 371
    • Fadel, A.1    Arzel, P.2
  • 21
    • 0005821348 scopus 로고
    • For nucleophilic addition of organocelium reagents to enolizable carbonyl compounds, see: Imamoto, T.; Kusumoto, T.; Tawaraya, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. See also: Jonson, C. R.; Tait, B. D. J. Org. Chem. 1987, 52, 281.
    • (1987) J. Org. Chem. , vol.52 , pp. 281
    • Jonson, C.R.1    Tait, B.D.2
  • 22
    • 0043258578 scopus 로고
    • For a review, see: B.M. Trost, I. Fleming, Heathcock C.H. Oxford: Pergamon
    • For a review, see: Kelly S.E. Trost B.M., Fleming I., Heathcock C.H. Comprehensive Organic Synthesis. 1:1991;743 Pergamon, Oxford.
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 743
    • Kelly, S.E.1
  • 24
    • 37049133608 scopus 로고
    • Baird, M. C.; Nyman, C. J.; Wilkinson, G. J. Chem. Soc. 1968, 348. See also: Sato, T.; Kugo, Y.; Nakaumi, E.; Ishibashi, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1995, 1801.
    • (1968) J. Chem. Soc. , pp. 348
    • Baird, M.C.1    Nyman, C.J.2    Wilkinson, G.3
  • 27
    • 0029843696 scopus 로고    scopus 로고
    • Barton, D. H. R.; Motherwell, W. B. Heterocycles 1984, 21, 1. See also: Campbell, J. A.; Rapoport, H. J. Org. Chem. 1996, 61, 6313.
    • (1996) J. Org. Chem. , vol.61 , pp. 6313
    • Campbell, J.A.1    Rapoport, H.2
  • 29
    • 0026319553 scopus 로고
    • For reductive methylation of a secondary amine with Raney nickel in methanol, see: François, D.; Lallemand, M.-C.; Selkti, M.; Tomas, A.; Kunesch, N.; Husson, H.-P. Angew. Chem., Int. Ed. 1998, 37, 104. See also: He, X.-S.; Brossi, A. J. Heterocycl. Chem. 1991, 28, 1741.
    • (1991) J. Heterocycl. Chem. , vol.28 , pp. 1741
    • He, X.-S.1    Brossi, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.