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Volumn 61, Issue 16, 1996, Pages 5418-5424

Stereoselective synthesis of (-)-α-kainic acid and (+)-α-allokainic acid via trimethylstannyl-mediated radical carbocyclization and oxidative destannylation

Author keywords

[No Author keywords available]

Indexed keywords

KAINIC ACID;

EID: 0029767411     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9604088     Document Type: Article
Times cited : (91)

References (60)
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    • references cited therein
    • Isolation from Digenea simplex : (a) Murukami, S.; Takemoto, T.; Shimizu, Z. J. Pharm. Soc. Jpn. 1953, 73, 1026. (b) Morimoto, H. J. Pharm. Soc. Jpn. 1965, 75, 766, 937. (c) Watase, H. Bull. Chem. Soc. Jpn. 1958, 31, 932 and references cited therein. Isolation from Centocerus clavulatrum: (d) Impellizzeri, G.; Mangiafico, S.; Oriente, G.; Piatelli, M.; Sciuto, S. Santacroce, C.; Sico, D. Phytochemistry 1975, 14, 1549. Isolation from Alsidium helmintrocarton: (e) Balansard, G.; Gayte-Sorbier, A.; Cavalli, C. Ann. Pharm. Fr., 1982, 40, 527.
    • (1958) Bull. Chem. Soc. Jpn. , vol.31 , pp. 932
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    • Isolation from Digenea simplex : (a) Murukami, S.; Takemoto, T.; Shimizu, Z. J. Pharm. Soc. Jpn. 1953, 73, 1026. (b) Morimoto, H. J. Pharm. Soc. Jpn. 1965, 75, 766, 937. (c) Watase, H. Bull. Chem. Soc. Jpn. 1958, 31, 932 and references cited therein. Isolation from Centocerus clavulatrum: (d) Impellizzeri, G.; Mangiafico, S.; Oriente, G.; Piatelli, M.; Sciuto, S. Santacroce, C.; Sico, D. Phytochemistry 1975, 14, 1549. Isolation from Alsidium helmintrocarton: (e) Balansard, G.; Gayte-Sorbier, A.; Cavalli, C. Ann. Pharm. Fr., 1982, 40, 527.
    • (1975) Phytochemistry , vol.14 , pp. 1549
    • Impellizzeri, G.1    Mangiafico, S.2    Oriente, G.3    Piatelli, M.4    Sciuto, S.5    Santacroce, C.6    Sico, D.7
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    • Isolation from Digenea simplex : (a) Murukami, S.; Takemoto, T.; Shimizu, Z. J. Pharm. Soc. Jpn. 1953, 73, 1026. (b) Morimoto, H. J. Pharm. Soc. Jpn. 1965, 75, 766, 937. (c) Watase, H. Bull. Chem. Soc. Jpn. 1958, 31, 932 and references cited therein. Isolation from Centocerus clavulatrum: (d) Impellizzeri, G.; Mangiafico, S.; Oriente, G.; Piatelli, M.; Sciuto, S. Santacroce, C.; Sico, D. Phytochemistry 1975, 14, 1549. Isolation from Alsidium helmintrocarton: (e) Balansard, G.; Gayte-Sorbier, A.; Cavalli, C. Ann. Pharm. Fr., 1982, 40, 527.
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    • Isolation: (a) Konno, K.; Shirahama, H.; Matsumoto, T. Tetrahedron Lett. 1983, 24, 939. Synthesis: (b) Konno, K.; Hoshimoto, K.; Ohfune, Y.; Shirahama, H.; Matsumoto, T. J. Am. Chem. Soc. 1988, 100, 4807. (c) Fushija, S.; Sato; Kanazawa, T.; Kusana, G.; Nozoe, S. Tetrahedron Lett. 1990, 31, 3901. (d) Baldwin, J. E.; Li, C.-S. J. Chem. Soc., Chem. Commun. 1988, 261.
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    • Isolation: (a) Konno, K.; Shirahama, H.; Matsumoto, T. Tetrahedron Lett. 1983, 24, 939. Synthesis: (b) Konno, K.; Hoshimoto, K.; Ohfune, Y.; Shirahama, H.; Matsumoto, T. J. Am. Chem. Soc. 1988, 100, 4807. (c) Fushija, S.; Sato; Kanazawa, T.; Kusana, G.; Nozoe, S. Tetrahedron Lett. 1990, 31, 3901. (d) Baldwin, J. E.; Li, C.-S. J. Chem. Soc., Chem. Commun. 1988, 261.
    • (1988) J. Am. Chem. Soc. , vol.100 , pp. 4807
    • Konno, K.1    Hoshimoto, K.2    Ohfune, Y.3    Shirahama, H.4    Matsumoto, T.5
  • 10
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    • Isolation: (a) Konno, K.; Shirahama, H.; Matsumoto, T. Tetrahedron Lett. 1983, 24, 939. Synthesis: (b) Konno, K.; Hoshimoto, K.; Ohfune, Y.; Shirahama, H.; Matsumoto, T. J. Am. Chem. Soc. 1988, 100, 4807. (c) Fushija, S.; Sato; Kanazawa, T.; Kusana, G.; Nozoe, S. Tetrahedron Lett. 1990, 31, 3901. (d) Baldwin, J. E.; Li, C.-S. J. Chem. Soc., Chem. Commun. 1988, 261.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 3901
    • Fushija, S.1    Sato2    Kanazawa, T.3    Kusana, G.4    Nozoe, S.5
  • 11
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    • Isolation: (a) Konno, K.; Shirahama, H.; Matsumoto, T. Tetrahedron Lett. 1983, 24, 939. Synthesis: (b) Konno, K.; Hoshimoto, K.; Ohfune, Y.; Shirahama, H.; Matsumoto, T. J. Am. Chem. Soc. 1988, 100, 4807. (c) Fushija, S.; Sato; Kanazawa, T.; Kusana, G.; Nozoe, S. Tetrahedron Lett. 1990, 31, 3901. (d) Baldwin, J. E.; Li, C.-S. J. Chem. Soc., Chem. Commun. 1988, 261.
    • (1988) J. Chem. Soc., Chem. Commun. , pp. 261
    • Baldwin, J.E.1    Li, C.-S.2
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    • Isolation: (a) Daigo, K. J. Pharm. Soc. Jpn. 1959, 79, 350. (b) Takemoto, T.; Daigo, K.; Kondo, Y.; Kondo, K. J. Pharm. Soc. Jpn. 1966, 86, 874. Synthesis: (c) Ohfune, Y.; Tomita, M. J. Am. Chem. Soc. 1982, 104, 3511. (d) Maeda, M.; Kodama, T.; Tanoka, T.; Yashimuzu, H.; Takemoto, T.; Nomoto, K.; Fujito, T. Tetrahedron Lett. 1987, 28, 633.
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    • Isolation: (a) Daigo, K. J. Pharm. Soc. Jpn. 1959, 79, 350. (b) Takemoto, T.; Daigo, K.; Kondo, Y.; Kondo, K. J. Pharm. Soc. Jpn. 1966, 86, 874. Synthesis: (c) Ohfune, Y.; Tomita, M. J. Am. Chem. Soc. 1982, 104, 3511. (d) Maeda, M.; Kodama, T.; Tanoka, T.; Yashimuzu, H.; Takemoto, T.; Nomoto, K.; Fujito, T. Tetrahedron Lett. 1987, 28, 633.
    • (1966) J. Pharm. Soc. Jpn. , vol.86 , pp. 874
    • Takemoto, T.1    Daigo, K.2    Kondo, Y.3    Kondo, K.4
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    • Isolation: (a) Daigo, K. J. Pharm. Soc. Jpn. 1959, 79, 350. (b) Takemoto, T.; Daigo, K.; Kondo, Y.; Kondo, K. J. Pharm. Soc. Jpn. 1966, 86, 874. Synthesis: (c) Ohfune, Y.; Tomita, M. J. Am. Chem. Soc. 1982, 104, 3511. (d) Maeda, M.; Kodama, T.; Tanoka, T.; Yashimuzu, H.; Takemoto, T.; Nomoto, K.; Fujito, T. Tetrahedron Lett. 1987, 28, 633.
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    • Ohfune, Y.1    Tomita, M.2
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    • Isolation: (a) Daigo, K. J. Pharm. Soc. Jpn. 1959, 79, 350. (b) Takemoto, T.; Daigo, K.; Kondo, Y.; Kondo, K. J. Pharm. Soc. Jpn. 1966, 86, 874. Synthesis: (c) Ohfune, Y.; Tomita, M. J. Am. Chem. Soc. 1982, 104, 3511. (d) Maeda, M.; Kodama, T.; Tanoka, T.; Yashimuzu, H.; Takemoto, T.; Nomoto, K.; Fujito, T. Tetrahedron Lett. 1987, 28, 633.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 633
    • Maeda, M.1    Kodama, T.2    Tanoka, T.3    Yashimuzu, H.4    Takemoto, T.5    Nomoto, K.6    Fujito, T.7
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    • (m) For reviews see: Synthesis of Optically Active α-Amino Acids; Williams, R. M., Ed.; Pergamon Press: New York, 1989; pp 305-380. Parsons, A. F. Tetrahedron 1996, 52, 4145.
    • (1996) Tetrahedron , vol.52 , pp. 4145
    • Parsons, A.F.1


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