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Volumn 43, Issue 38, 2002, Pages 6739-6741

A new and efficient synthesis of (-)-indolizidine 167B by tandem metathesis

Author keywords

Asymmetric synthesis; Heterocycles; Rearrangement; Ruthenium

Indexed keywords

CYCLOHEPTENE; INDOLIZIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; RUTHENIUM;

EID: 0037119739     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01534-4     Document Type: Article
Times cited : (40)

References (28)
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    • For recent syntheses of (-)-indolizidine 167B (1), see: (a) Corvo, M. C.; Pareira, M. M. A. Tetrahedron Lett. 2002, 43, 455-458; (b) Kim, G.; Lee, E.-J. Tetrahedron: Asymmetry 2001, 12, 2073-2076; © Peroche, S.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J.-C. Tetrahedron Lett. 2001, 42, 4617-4619; (d) Ma, D.; Sun, H. Org. Lett. 2000, 2, 2503-2505; (e) Bach, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543-4552; (f) Yamazaki, N.; Ito, T.; Kibayashi, C. Org. Lett. 2000, 2, 465-467; (g) Chalard, P.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J.-C.; Canet, I. Tetrahedron Lett. 1999, 40, 1661-1664.
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    • For recent syntheses of (-)-indolizidine 167B (1), see: (a) Corvo, M. C.; Pareira, M. M. A. Tetrahedron Lett. 2002, 43, 455-458; (b) Kim, G.; Lee, E.-J. Tetrahedron: Asymmetry 2001, 12, 2073-2076; © Peroche, S.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J.-C. Tetrahedron Lett. 2001, 42, 4617-4619; (d) Ma, D.; Sun, H. Org. Lett. 2000, 2, 2503-2505; (e) Bach, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543-4552; (f) Yamazaki, N.; Ito, T.; Kibayashi, C. Org. Lett. 2000, 2, 465-467; (g) Chalard, P.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J.-C.; Canet, I. Tetrahedron Lett. 1999, 40, 1661-1664.
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    • For recent syntheses of (-)-indolizidine 167B (1), see: (a) Corvo, M. C.; Pareira, M. M. A. Tetrahedron Lett. 2002, 43, 455-458; (b) Kim, G.; Lee, E.-J. Tetrahedron: Asymmetry 2001, 12, 2073-2076; © Peroche, S.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J.-C. Tetrahedron Lett. 2001, 42, 4617-4619; (d) Ma, D.; Sun, H. Org. Lett. 2000, 2, 2503-2505; (e) Bach, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543-4552; (f) Yamazaki, N.; Ito, T.; Kibayashi, C. Org. Lett. 2000, 2, 465-467; (g) Chalard, P.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J.-C.; Canet, I. Tetrahedron Lett. 1999, 40, 1661-1664.
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    • For recent syntheses of (-)-indolizidine 167B (1), see: (a) Corvo, M. C.; Pareira, M. M. A. Tetrahedron Lett. 2002, 43, 455-458; (b) Kim, G.; Lee, E.-J. Tetrahedron: Asymmetry 2001, 12, 2073-2076; © Peroche, S.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J.-C. Tetrahedron Lett. 2001, 42, 4617-4619; (d) Ma, D.; Sun, H. Org. Lett. 2000, 2, 2503-2505; (e) Bach, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543-4552; (f) Yamazaki, N.; Ito, T.; Kibayashi, C. Org. Lett. 2000, 2, 465-467; (g) Chalard, P.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J.-C.; Canet, I. Tetrahedron Lett. 1999, 40, 1661-1664.
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    • Ma, D.1    Sun, H.2
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    • For recent syntheses of (-)-indolizidine 167B (1), see: (a) Corvo, M. C.; Pareira, M. M. A. Tetrahedron Lett. 2002, 43, 455-458; (b) Kim, G.; Lee, E.-J. Tetrahedron: Asymmetry 2001, 12, 2073-2076; © Peroche, S.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J.-C. Tetrahedron Lett. 2001, 42, 4617-4619; (d) Ma, D.; Sun, H. Org. Lett. 2000, 2, 2503-2505; (e) Bach, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543-4552; (f) Yamazaki, N.; Ito, T.; Kibayashi, C. Org. Lett. 2000, 2, 465-467; (g) Chalard, P.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J.-C.; Canet, I. Tetrahedron Lett. 1999, 40, 1661-1664.
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    • Bach, T.G.1    Nakajima, K.J.2
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    • For recent syntheses of (-)-indolizidine 167B (1), see: (a) Corvo, M. C.; Pareira, M. M. A. Tetrahedron Lett. 2002, 43, 455-458; (b) Kim, G.; Lee, E.-J. Tetrahedron: Asymmetry 2001, 12, 2073-2076; © Peroche, S.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J.-C. Tetrahedron Lett. 2001, 42, 4617-4619; (d) Ma, D.; Sun, H. Org. Lett. 2000, 2, 2503-2505; (e) Bach, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543-4552; (f) Yamazaki, N.; Ito, T.; Kibayashi, C. Org. Lett. 2000, 2, 465-467; (g) Chalard, P.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J.-C.; Canet, I. Tetrahedron Lett. 1999, 40, 1661-1664.
    • (2000) Org. Lett. , vol.2 , pp. 465-467
    • Yamazaki, N.1    Ito, T.2    Kibayashi, C.3
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    • 0033605165 scopus 로고    scopus 로고
    • For recent syntheses of (-)-indolizidine 167B (1), see: (a) Corvo, M. C.; Pareira, M. M. A. Tetrahedron Lett. 2002, 43, 455-458; (b) Kim, G.; Lee, E.-J. Tetrahedron: Asymmetry 2001, 12, 2073-2076; © Peroche, S.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J.-C. Tetrahedron Lett. 2001, 42, 4617-4619; (d) Ma, D.; Sun, H. Org. Lett. 2000, 2, 2503-2505; (e) Bach, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543-4552; (f) Yamazaki, N.; Ito, T.; Kibayashi, C. Org. Lett. 2000, 2, 465-467; (g) Chalard, P.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J.-C.; Canet, I. Tetrahedron Lett. 1999, 40, 1661-1664.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 1661-1664
    • Chalard, P.1    Remuson, R.2    Gelas-Mialhe, Y.3    Gramain, J.-C.4    Canet, I.5
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    • A similar strategy was applied in the synthesis of (-)-halosaline. See: Stragies R., Blechert S. Tetrahedron. 55:1999;8179-8188.
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    • Stragies, R.1    Blechert, S.2


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