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Volumn 11, Issue 6, 2000, Pages 1405-1410

A new and efficient synthetic route to enantiopure (+)-anatoxin-a from (-)-cocaine hydrochloride

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; ANATOXIN A; BICYCLO[3.3.1]NONANE DERIVATIVE; COCAINE; ETHER; NICOTINIC AGENT; PALLADIUM; TRIFLUOROMETHANESULFONIC ACID; TROPANE DERIVATIVE; VINYL DERIVATIVE;

EID: 0034616241     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00059-8     Document Type: Article
Times cited : (41)

References (23)
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    • For the most recent syntheses, see: (a) Parsons, P. J.; Camp, N. P.; Edwards, N.; Sumoreeah, L. R. Tetrahedron 2000, 56, 309-315; (b) Aggarwal, V. L.; Humphries, P. S.; Fenwick. A. Angew. Chem. 1999, 111, 2178-2180; Angew. Chem., Int. Ed. Engl. 1999, 38, 1985-1986; (c) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057-3064; (d) Oh, C.-Y.; Kim, K.-S.; Ham, W.-A.; Tetrahedron Lett. 1998, 39, 2133-2136; (e) Magnus, N. A.; Ducry, L.; Rolland, V.; Wonnacott, S.; Gallagher, T. J. Chem. Soc., Perkin Trans. 1 1997, 2313-2318; (f) Parsons, P. J.; Camp. N. P.; Underwood, J. M.; Harvey, D. M. Tetrahedron 1996, 52, 11637-11642; (g) Newcombe, N. J.; Simpkins, N. S. J. Chem. Soc., Chem. Commun. 1995, 831-832; (h) Hernandez, A.; Rapoport, H. J. Org. Chem. 1994, 59, 1058-1066; (i) Sardine, F. J.; Howard, M. H.; Morningstar, M.; Rapoport, H. J. Org. Chem. 1990, 55, 5025-5033; (j) Koskinen, A. M. P.; Rapoport, H. J. Med. Chem. 1985, 28, 1301-1309.
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    • For the most recent syntheses, see: (a) Parsons, P. J.; Camp, N. P.; Edwards, N.; Sumoreeah, L. R. Tetrahedron 2000, 56, 309-315; (b) Aggarwal, V. L.; Humphries, P. S.; Fenwick. A. Angew. Chem. 1999, 111, 2178-2180; Angew. Chem., Int. Ed. Engl. 1999, 38, 1985-1986; (c) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057-3064; (d) Oh, C.-Y.; Kim, K.-S.; Ham, W.-A.; Tetrahedron Lett. 1998, 39, 2133-2136; (e) Magnus, N. A.; Ducry, L.; Rolland, V.; Wonnacott, S.; Gallagher, T. J. Chem. Soc., Perkin Trans. 1 1997, 2313-2318; (f) Parsons, P. J.; Camp. N. P.; Underwood, J. M.; Harvey, D. M. Tetrahedron 1996, 52, 11637-11642; (g) Newcombe, N. J.; Simpkins, N. S. J. Chem. Soc., Chem. Commun. 1995, 831-832; (h) Hernandez, A.; Rapoport, H. J. Org. Chem. 1994, 59, 1058-1066; (i) Sardine, F. J.; Howard, M. H.; Morningstar, M.; Rapoport, H. J. Org. Chem. 1990, 55, 5025-5033; (j) Koskinen, A. M. P.; Rapoport, H. J. Med. Chem. 1985, 28, 1301-1309.
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    • For the most recent syntheses, see: (a) Parsons, P. J.; Camp, N. P.; Edwards, N.; Sumoreeah, L. R. Tetrahedron 2000, 56, 309-315; (b) Aggarwal, V. L.; Humphries, P. S.; Fenwick. A. Angew. Chem. 1999, 111, 2178-2180; Angew. Chem., Int. Ed. Engl. 1999, 38, 1985-1986; (c) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057-3064; (d) Oh, C.-Y.; Kim, K.-S.; Ham, W.-A.; Tetrahedron Lett. 1998, 39, 2133-2136; (e) Magnus, N. A.; Ducry, L.; Rolland, V.; Wonnacott, S.; Gallagher, T. J. Chem. Soc., Perkin Trans. 1 1997, 2313-2318; (f) Parsons, P. J.; Camp. N. P.; Underwood, J. M.; Harvey, D. M. Tetrahedron 1996, 52, 11637-11642; (g) Newcombe, N. J.; Simpkins, N. S. J. Chem. Soc., Chem. Commun. 1995, 831-832; (h) Hernandez, A.; Rapoport, H. J. Org. Chem. 1994, 59, 1058-1066; (i) Sardine, F. J.; Howard, M. H.; Morningstar, M.; Rapoport, H. J. Org. Chem. 1990, 55, 5025-5033; (j) Koskinen, A. M. P.; Rapoport, H. J. Med. Chem. 1985, 28, 1301-1309.
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    • For the most recent syntheses, see: (a) Parsons, P. J.; Camp, N. P.; Edwards, N.; Sumoreeah, L. R. Tetrahedron 2000, 56, 309-315; (b) Aggarwal, V. L.; Humphries, P. S.; Fenwick. A. Angew. Chem. 1999, 111, 2178-2180; Angew. Chem., Int. Ed. Engl. 1999, 38, 1985-1986; (c) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057-3064; (d) Oh, C.-Y.; Kim, K.-S.; Ham, W.-A.; Tetrahedron Lett. 1998, 39, 2133-2136; (e) Magnus, N. A.; Ducry, L.; Rolland, V.; Wonnacott, S.; Gallagher, T. J. Chem. Soc., Perkin Trans. 1 1997, 2313-2318; (f) Parsons, P. J.; Camp. N. P.; Underwood, J. M.; Harvey, D. M. Tetrahedron 1996, 52, 11637-11642; (g) Newcombe, N. J.; Simpkins, N. S. J. Chem. Soc., Chem. Commun. 1995, 831-832; (h) Hernandez, A.; Rapoport, H. J. Org. Chem. 1994, 59, 1058-1066; (i) Sardine, F. J.; Howard, M. H.; Morningstar, M.; Rapoport, H. J. Org. Chem. 1990, 55, 5025-5033; (j) Koskinen, A. M. P.; Rapoport, H. J. Med. Chem. 1985, 28, 1301-1309.
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    • For the most recent syntheses, see: (a) Parsons, P. J.; Camp, N. P.; Edwards, N.; Sumoreeah, L. R. Tetrahedron 2000, 56, 309-315; (b) Aggarwal, V. L.; Humphries, P. S.; Fenwick. A. Angew. Chem. 1999, 111, 2178-2180; Angew. Chem., Int. Ed. Engl. 1999, 38, 1985-1986; (c) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057-3064; (d) Oh, C.-Y.; Kim, K.-S.; Ham, W.-A.; Tetrahedron Lett. 1998, 39, 2133-2136; (e) Magnus, N. A.; Ducry, L.; Rolland, V.; Wonnacott, S.; Gallagher, T. J. Chem. Soc., Perkin Trans. 1 1997, 2313-2318; (f) Parsons, P. J.; Camp. N. P.; Underwood, J. M.; Harvey, D. M. Tetrahedron 1996, 52, 11637-11642; (g) Newcombe, N. J.; Simpkins, N. S. J. Chem. Soc., Chem. Commun. 1995, 831-832; (h) Hernandez, A.; Rapoport, H. J. Org. Chem. 1994, 59, 1058-1066; (i) Sardine, F. J.; Howard, M. H.; Morningstar, M.; Rapoport, H. J. Org. Chem. 1990, 55, 5025-5033; (j) Koskinen, A. M. P.; Rapoport, H. J. Med. Chem. 1985, 28, 1301-1309.
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    • Parsons, P.J.1    Camp, N.P.2    Underwood, J.M.3    Harvey, D.M.4
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    • 0029026296 scopus 로고
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    • For the most recent syntheses, see: (a) Parsons, P. J.; Camp, N. P.; Edwards, N.; Sumoreeah, L. R. Tetrahedron 2000, 56, 309-315; (b) Aggarwal, V. L.; Humphries, P. S.; Fenwick. A. Angew. Chem. 1999, 111, 2178-2180; Angew. Chem., Int. Ed. Engl. 1999, 38, 1985-1986; (c) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057-3064; (d) Oh, C.-Y.; Kim, K.-S.; Ham, W.-A.; Tetrahedron Lett. 1998, 39, 2133-2136; (e) Magnus, N. A.; Ducry, L.; Rolland, V.; Wonnacott, S.; Gallagher, T. J. Chem. Soc., Perkin Trans. 1 1997, 2313-2318; (f) Parsons, P. J.; Camp. N. P.; Underwood, J. M.; Harvey, D. M. Tetrahedron 1996, 52, 11637-11642; (g) Newcombe, N. J.; Simpkins, N. S. J. Chem. Soc., Chem. Commun. 1995, 831-832; (h) Hernandez, A.; Rapoport, H. J. Org. Chem. 1994, 59, 1058-1066; (i) Sardine, F. J.; Howard, M. H.; Morningstar, M.; Rapoport, H. J. Org. Chem. 1990, 55, 5025-5033; (j) Koskinen, A. M. P.; Rapoport, H. J. Med. Chem. 1985, 28, 1301-1309.
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    • For the most recent syntheses, see: (a) Parsons, P. J.; Camp, N. P.; Edwards, N.; Sumoreeah, L. R. Tetrahedron 2000, 56, 309-315; (b) Aggarwal, V. L.; Humphries, P. S.; Fenwick. A. Angew. Chem. 1999, 111, 2178-2180; Angew. Chem., Int. Ed. Engl. 1999, 38, 1985-1986; (c) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057-3064; (d) Oh, C.-Y.; Kim, K.-S.; Ham, W.-A.; Tetrahedron Lett. 1998, 39, 2133-2136; (e) Magnus, N. A.; Ducry, L.; Rolland, V.; Wonnacott, S.; Gallagher, T. J. Chem. Soc., Perkin Trans. 1 1997, 2313-2318; (f) Parsons, P. J.; Camp. N. P.; Underwood, J. M.; Harvey, D. M. Tetrahedron 1996, 52, 11637-11642; (g) Newcombe, N. J.; Simpkins, N. S. J. Chem. Soc., Chem. Commun. 1995, 831-832; (h) Hernandez, A.; Rapoport, H. J. Org. Chem. 1994, 59, 1058-1066; (i) Sardine, F. J.; Howard, M. H.; Morningstar, M.; Rapoport, H. J. Org. Chem. 1990, 55, 5025-5033; (j) Koskinen, A. M. P.; Rapoport, H. J. Med. Chem. 1985, 28, 1301-1309.
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    • For the most recent syntheses, see: (a) Parsons, P. J.; Camp, N. P.; Edwards, N.; Sumoreeah, L. R. Tetrahedron 2000, 56, 309-315; (b) Aggarwal, V. L.; Humphries, P. S.; Fenwick. A. Angew. Chem. 1999, 111, 2178-2180; Angew. Chem., Int. Ed. Engl. 1999, 38, 1985-1986; (c) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057-3064; (d) Oh, C.-Y.; Kim, K.-S.; Ham, W.-A.; Tetrahedron Lett. 1998, 39, 2133-2136; (e) Magnus, N. A.; Ducry, L.; Rolland, V.; Wonnacott, S.; Gallagher, T. J. Chem. Soc., Perkin Trans. 1 1997, 2313-2318; (f) Parsons, P. J.; Camp. N. P.; Underwood, J. M.; Harvey, D. M. Tetrahedron 1996, 52, 11637-11642; (g) Newcombe, N. J.; Simpkins, N. S. J. Chem. Soc., Chem. Commun. 1995, 831-832; (h) Hernandez, A.; Rapoport, H. J. Org. Chem. 1994, 59, 1058-1066; (i) Sardine, F. J.; Howard, M. H.; Morningstar, M.; Rapoport, H. J. Org. Chem. 1990, 55, 5025-5033; (j) Koskinen, A. M. P.; Rapoport, H. J. Med. Chem. 1985, 28, 1301-1309.
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    • For the most recent syntheses, see: (a) Parsons, P. J.; Camp, N. P.; Edwards, N.; Sumoreeah, L. R. Tetrahedron 2000, 56, 309-315; (b) Aggarwal, V. L.; Humphries, P. S.; Fenwick. A. Angew. Chem. 1999, 111, 2178-2180; Angew. Chem., Int. Ed. Engl. 1999, 38, 1985-1986; (c) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057-3064; (d) Oh, C.-Y.; Kim, K.-S.; Ham, W.-A.; Tetrahedron Lett. 1998, 39, 2133-2136; (e) Magnus, N. A.; Ducry, L.; Rolland, V.; Wonnacott, S.; Gallagher, T. J. Chem. Soc., Perkin Trans. 1 1997, 2313-2318; (f) Parsons, P. J.; Camp. N. P.; Underwood, J. M.; Harvey, D. M. Tetrahedron 1996, 52, 11637-11642; (g) Newcombe, N. J.; Simpkins, N. S. J. Chem. Soc., Chem. Commun. 1995, 831-832; (h) Hernandez, A.; Rapoport, H. J. Org. Chem. 1994, 59, 1058-1066; (i) Sardine, F. J.; Howard, M. H.; Morningstar, M.; Rapoport, H. J. Org. Chem. 1990, 55, 5025-5033; (j) Koskinen, A. M. P.; Rapoport, H. J. Med. Chem. 1985, 28, 1301-1309.
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    • For recent reviews on nAChRs as targets for drug discovery, see: (a)
    • For recent reviews on nAChRs as targets for drug discovery, see: (a) Holladay, M. W.; Dart, M. J.; Lynch, J. K. J. Med. Chem. 1998, 40, 4169-4194; (b) Holladay, M. W.; Lebold, S. A.; Lin, N.-H. Drug Dev. Res. 1995, 35, 191-213.
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    • For recent reviews on nAChRs as targets for drug discovery, see: (a) Holladay, M. W.; Dart, M. J.; Lynch, J. K. J. Med. Chem. 1998, 40, 4169-4194; (b) Holladay, M. W.; Lebold, S. A.; Lin, N.-H. Drug Dev. Res. 1995, 35, 191-213.
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    • For leading references, see: (a) Podlech, J.; J. Prakt. Chem. 1998, 340, 679-682; (b) Yang, S.; Hungerhoff, B.; Metz, P.; Tetrahedron Lett. 1998, 39, 2097-2098.
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    • For leading references, see: (a) Podlech, J.; J. Prakt. Chem. 1998, 340, 679-682; (b) Yang, S.; Hungerhoff, B.; Metz, P.; Tetrahedron Lett. 1998, 39, 2097-2098.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 2097-2098
    • Yang, S.1    Hungerhoff, B.2    Metz, P.3


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