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Volumn 120, Issue 11, 1998, Pages 2543-2552

Total synthesis of spinosyn A. 1. Enantioselective construction of a key tricyclic intermediate by a multiple configurational inversion scheme

Author keywords

[No Author keywords available]

Indexed keywords

INSECTICIDE; SPINOSYN A; UNCLASSIFIED DRUG;

EID: 0032565075     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja974009l     Document Type: Article
Times cited : (86)

References (48)
  • 4
    • 15444376147 scopus 로고
    • Boeck, L. D.; Chio, E. H.; Eaton, T. E.; Godfrey, O. W.; Michel, K. H.; Nakatsukasa, W. M.; Yao, R. C. Eur. Pat. Appl. 375316, 1990; Chem. Abstr. 1991, 114, 80066.
    • (1991) Chem. Abstr. , vol.114 , pp. 80066
  • 7
    • 0000488068 scopus 로고
    • American Chemical Society: Washington. DC, and references therein
    • Kirst, H. A.; Michel, K. H.; Mynderase, J. C.; Chio, E. H.; Yao, R. C.; Natsukasa, W. M.; Boeck, L. D.; Occolowitz, J. L.; Paschal, J. W.; Deeter, J. B.; Thompson, G. D. In Synthesis and Chemistry of Agrochemicals III; Baker, D. R., Fenyes, J. G., Steffens, J. J., Eds.; ACS Symposium Series No. 504; American Chemical Society: Washington. DC, 1992; pp 214-215 and references therein.
    • (1992) ACS Symposium Series No. 504 , pp. 214-215
    • Baker, D.R.1    Fenyes, J.G.2    Steffens, J.J.3
  • 8
    • 2642651986 scopus 로고    scopus 로고
    • note
    • The names initially adopted for 1 (LY232105, A83543A, and lepicidin A) have been recently abandoned in favor of spinosyn A (Kirst, H. A.; communication dated June 7, 1994).
  • 11
    • 2642676149 scopus 로고
    • Evans, D. A.; Black, W. C. J. Am. Chem. Soc. 1992, 114, 2260; 1993, 115, 4497.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 4497
  • 13
    • 0015345302 scopus 로고
    • Isolation: (a) Jomon, K.; Kuroda, Y.; Ajisaka, M.; Sakai, H. J. Antibiot. 1972, 25, 271. (b) Ito, S.; Hirata, Y. Tetrahedron Lett. 1972, 1181, 1185, 2257. (c) Ito, S.; Hirata, Y. Bull. Chem. Soc. Jpn. 1977, 50, 227, 1813.
    • (1972) J. Antibiot. , vol.25 , pp. 271
    • Jomon, K.1    Kuroda, Y.2    Ajisaka, M.3    Sakai, H.4
  • 14
    • 0000950957 scopus 로고
    • Isolation: (a) Jomon, K.; Kuroda, Y.; Ajisaka, M.; Sakai, H. J. Antibiot. 1972, 25, 271. (b) Ito, S.; Hirata, Y. Tetrahedron Lett. 1972, 1181, 1185, 2257. (c) Ito, S.; Hirata, Y. Bull. Chem. Soc. Jpn. 1977, 50, 227, 1813.
    • (1972) Tetrahedron Lett. , vol.1181 , pp. 1185
    • Ito, S.1    Hirata, Y.2
  • 15
    • 0017710502 scopus 로고
    • Isolation: (a) Jomon, K.; Kuroda, Y.; Ajisaka, M.; Sakai, H. J. Antibiot. 1972, 25, 271. (b) Ito, S.; Hirata, Y. Tetrahedron Lett. 1972, 1181, 1185, 2257. (c) Ito, S.; Hirata, Y. Bull. Chem. Soc. Jpn. 1977, 50, 227, 1813.
    • (1977) Bull. Chem. Soc. Jpn. , vol.50 , pp. 227
    • Ito, S.1    Hirata, Y.2
  • 16
    • 0024422299 scopus 로고
    • Total synthesis: (a) Boeckman, R. K., Jr.; Weidner, C. H.; Perni, R. B.; Napier, J. J. J. Am. Chem. Soc. 1989, 111, 8036. (b) Paquette, L. A.; Macdonald, D.; Anderson, L. G.; Wright, J. J. Am. Chem. Soc. 1989, 111, 8037. (c) Paquette, L. A.; Romine, J. L.; Lin, H. S.; Wright, J. J. Am. Chem. Soc. 1990, 112, 9284. (d) Paquette, L. A.; Macdonald, D.; Anderson, L. G. J. Am. Chem. Soc. 1990, 112, 9292. (e) Roush, W. R.; Wada, C. K. J. Am. Chem. Soc. 1994, 116, 2151.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 8036
    • Boeckman Jr., R.K.1    Weidner, C.H.2    Perni, R.B.3    Napier, J.J.4
  • 17
    • 0024451471 scopus 로고
    • Total synthesis: (a) Boeckman, R. K., Jr.; Weidner, C. H.; Perni, R. B.; Napier, J. J. J. Am. Chem. Soc. 1989, 111, 8036. (b) Paquette, L. A.; Macdonald, D.; Anderson, L. G.; Wright, J. J. Am. Chem. Soc. 1989, 111, 8037. (c) Paquette, L. A.; Romine, J. L.; Lin, H. S.; Wright, J. J. Am. Chem. Soc. 1990, 112, 9284. (d) Paquette, L. A.; Macdonald, D.; Anderson, L. G. J. Am. Chem. Soc. 1990, 112, 9292. (e) Roush, W. R.; Wada, C. K. J. Am. Chem. Soc. 1994, 116, 2151.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 8037
    • Paquette, L.A.1    Macdonald, D.2    Anderson, L.G.3    Wright, J.4
  • 18
    • 0025684593 scopus 로고
    • Total synthesis: (a) Boeckman, R. K., Jr.; Weidner, C. H.; Perni, R. B.; Napier, J. J. J. Am. Chem. Soc. 1989, 111, 8036. (b) Paquette, L. A.; Macdonald, D.; Anderson, L. G.; Wright, J. J. Am. Chem. Soc. 1989, 111, 8037. (c) Paquette, L. A.; Romine, J. L.; Lin, H. S.; Wright, J. J. Am. Chem. Soc. 1990, 112, 9284. (d) Paquette, L. A.; Macdonald, D.; Anderson, L. G. J. Am. Chem. Soc. 1990, 112, 9292. (e) Roush, W. R.; Wada, C. K. J. Am. Chem. Soc. 1994, 116, 2151.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 9284
    • Paquette, L.A.1    Romine, J.L.2    Lin, H.S.3    Wright, J.4
  • 19
    • 0025607770 scopus 로고
    • Total synthesis: (a) Boeckman, R. K., Jr.; Weidner, C. H.; Perni, R. B.; Napier, J. J. J. Am. Chem. Soc. 1989, 111, 8036. (b) Paquette, L. A.; Macdonald, D.; Anderson, L. G.; Wright, J. J. Am. Chem. Soc. 1989, 111, 8037. (c) Paquette, L. A.; Romine, J. L.; Lin, H. S.; Wright, J. J. Am. Chem. Soc. 1990, 112, 9284. (d) Paquette, L. A.; Macdonald, D.; Anderson, L. G. J. Am. Chem. Soc. 1990, 112, 9292. (e) Roush, W. R.; Wada, C. K. J. Am. Chem. Soc. 1994, 116, 2151.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 9292
    • Paquette, L.A.1    Macdonald, D.2    Anderson, L.G.3
  • 20
    • 0027971089 scopus 로고
    • Total synthesis: (a) Boeckman, R. K., Jr.; Weidner, C. H.; Perni, R. B.; Napier, J. J. J. Am. Chem. Soc. 1989, 111, 8036. (b) Paquette, L. A.; Macdonald, D.; Anderson, L. G.; Wright, J. J. Am. Chem. Soc. 1989, 111, 8037. (c) Paquette, L. A.; Romine, J. L.; Lin, H. S.; Wright, J. J. Am. Chem. Soc. 1990, 112, 9284. (d) Paquette, L. A.; Macdonald, D.; Anderson, L. G. J. Am. Chem. Soc. 1990, 112, 9292. (e) Roush, W. R.; Wada, C. K. J. Am. Chem. Soc. 1994, 116, 2151.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 2151
    • Roush, W.R.1    Wada, C.K.2
  • 23
    • 0242597961 scopus 로고
    • (b) Seto, H.; Yonehara, H.; Aizawa, S.; Akutsu, H.; Clardy, J.; Arnold, E.; Tanabe, M.; Urano, S. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1979, 394; Chem. Abstr. 1980, 92, 211459u.
    • (1980) Chem. Abstr. , vol.92
  • 42
    • 2642619517 scopus 로고    scopus 로고
    • note
    • (b) Under these circumstances, four isomers were produced in a 40:12:9:39 ratio and isolated in a combined 60% yield. The first of these products was subsequently identified as 25. All four gave the same molecular ion peak in high resoluton MS.
  • 44
    • 2642618712 scopus 로고
    • Paquette, L. A., Ed.; J. Wiley and Sons, Inc.; Chichester, England
    • (b) This effect can be attributed to the in situ generation of a different borane species. For a summary of past observations, consult Banfi, L.; Narisano, E.; Riva, R. Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; J. Wiley and Sons, Inc.; Chichester, England; 1995; Volume 5, pp 3046-3049.
    • (1995) Encyclopedia of Reagents for Organic Synthesis , vol.5 , pp. 3046-3049
    • Banfi, L.1    Narisano, E.2    Riva, R.3


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