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Volumn 67, Issue 20, 2002, Pages 6954-6959

A short synthesis of (+)-narciclasine via a strategy derived from stereocontrolled epoxide formation and SnCl4-catalyzed arene-epoxide coupling

Author keywords

[No Author keywords available]

Indexed keywords

RING SYSTEMS;

EID: 0037019967     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020155k     Document Type: Article
Times cited : (62)

References (43)
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    • (d) Extensive studies have revealed that camphor-based chloronitroso 9 has shown exceptionally high stereoselection in cycloadditions. Elango, S.; Wang, Y.-C.; Cheng, C.-L.; Yan, T.-H. Tetrahedron Lett. 2002, 43, 3757.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 3757
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    • For chloronitroso dienophiles derived from steroid, D-mannofuranose, D-xylofuranose, L-xylose, and D-xylose, see: (a) Iida, H.; Watanabe, Y.; Kibayashi, C. Tetrahedron, Lett. 1984, 31, 5091. (b) Schurrle, K.; Beier, B.; Piepersberg, W. J. Chem. Soc., Perkin Trans. 1 1991, 2407. (c) Braun, H.; Felber, H.; Kresze, G.; Schmidtchen, F. P.; Prewo, R.; Vasella, A. Liebigs Ann. Chem. 1993, 261, and earlier references therein. (d) Adrian, H.; Bailey, P. D.; Rees, D. C.; Wightman, R. H. J. Chem. Soc., Chem. Commun. 1998, 2251. (e) Faitg, T.; Soulie, J.; Lallemand J.-Y.; Ricard, L. Tetrahedron: Asymmetry 1999, 2165. (f) Hall, A.; Bailey, P. D.; Rees, D. C.; Rosair, G. M.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 2000, 329.
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    • For chloronitroso dienophiles derived from steroid, D-mannofuranose, D-xylofuranose, L-xylose, and D-xylose, see: (a) Iida, H.; Watanabe, Y.; Kibayashi, C. Tetrahedron, Lett. 1984, 31, 5091. (b) Schurrle, K.; Beier, B.; Piepersberg, W. J. Chem. Soc., Perkin Trans. 1 1991, 2407. (c) Braun, H.; Felber, H.; Kresze, G.; Schmidtchen, F. P.; Prewo, R.; Vasella, A. Liebigs Ann. Chem. 1993, 261, and earlier references therein. (d) Adrian, H.; Bailey, P. D.; Rees, D. C.; Wightman, R. H. J. Chem. Soc., Chem. Commun. 1998, 2251. (e) Faitg, T.; Soulie, J.; Lallemand J.-Y.; Ricard, L. Tetrahedron: Asymmetry 1999, 2165. (f) Hall, A.; Bailey, P. D.; Rees, D. C.; Rosair, G. M.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 2000, 329.
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    • and earlier references therein
    • For chloronitroso dienophiles derived from steroid, D-mannofuranose, D-xylofuranose, L-xylose, and D-xylose, see: (a) Iida, H.; Watanabe, Y.; Kibayashi, C. Tetrahedron, Lett. 1984, 31, 5091. (b) Schurrle, K.; Beier, B.; Piepersberg, W. J. Chem. Soc., Perkin Trans. 1 1991, 2407. (c) Braun, H.; Felber, H.; Kresze, G.; Schmidtchen, F. P.; Prewo, R.; Vasella, A. Liebigs Ann. Chem. 1993, 261, and earlier references therein. (d) Adrian, H.; Bailey, P. D.; Rees, D. C.; Wightman, R. H. J. Chem. Soc., Chem. Commun. 1998, 2251. (e) Faitg, T.; Soulie, J.; Lallemand J.-Y.; Ricard, L. Tetrahedron: Asymmetry 1999, 2165. (f) Hall, A.; Bailey, P. D.; Rees, D. C.; Rosair, G. M.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 2000, 329.
    • (1993) Liebigs Ann. Chem. , vol.261
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    • For chloronitroso dienophiles derived from steroid, D-mannofuranose, D-xylofuranose, L-xylose, and D-xylose, see: (a) Iida, H.; Watanabe, Y.; Kibayashi, C. Tetrahedron, Lett. 1984, 31, 5091. (b) Schurrle, K.; Beier, B.; Piepersberg, W. J. Chem. Soc., Perkin Trans. 1 1991, 2407. (c) Braun, H.; Felber, H.; Kresze, G.; Schmidtchen, F. P.; Prewo, R.; Vasella, A. Liebigs Ann. Chem. 1993, 261, and earlier references therein. (d) Adrian, H.; Bailey, P. D.; Rees, D. C.; Wightman, R. H. J. Chem. Soc., Chem. Commun. 1998, 2251. (e) Faitg, T.; Soulie, J.; Lallemand J.-Y.; Ricard, L. Tetrahedron: Asymmetry 1999, 2165. (f) Hall, A.; Bailey, P. D.; Rees, D. C.; Rosair, G. M.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 2000, 329.
    • (1998) J. Chem. Soc., Chem. Commun. , vol.2251
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    • For chloronitroso dienophiles derived from steroid, D-mannofuranose, D-xylofuranose, L-xylose, and D-xylose, see: (a) Iida, H.; Watanabe, Y.; Kibayashi, C. Tetrahedron, Lett. 1984, 31, 5091. (b) Schurrle, K.; Beier, B.; Piepersberg, W. J. Chem. Soc., Perkin Trans. 1 1991, 2407. (c) Braun, H.; Felber, H.; Kresze, G.; Schmidtchen, F. P.; Prewo, R.; Vasella, A. Liebigs Ann. Chem. 1993, 261, and earlier references therein. (d) Adrian, H.; Bailey, P. D.; Rees, D. C.; Wightman, R. H. J. Chem. Soc., Chem. Commun. 1998, 2251. (e) Faitg, T.; Soulie, J.; Lallemand J.-Y.; Ricard, L. Tetrahedron: Asymmetry 1999, 2165. (f) Hall, A.; Bailey, P. D.; Rees, D. C.; Rosair, G. M.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 2000, 329.
    • (1999) Tetrahedron: Asymmetry , vol.2165
    • Faitg, T.1    Soulie, J.2    Lallemand, J.-Y.3    Ricard, L.4
  • 29
    • 0034615207 scopus 로고    scopus 로고
    • For chloronitroso dienophiles derived from steroid, D-mannofuranose, D-xylofuranose, L-xylose, and D-xylose, see: (a) Iida, H.; Watanabe, Y.; Kibayashi, C. Tetrahedron, Lett. 1984, 31, 5091. (b) Schurrle, K.; Beier, B.; Piepersberg, W. J. Chem. Soc., Perkin Trans. 1 1991, 2407. (c) Braun, H.; Felber, H.; Kresze, G.; Schmidtchen, F. P.; Prewo, R.; Vasella, A. Liebigs Ann. Chem. 1993, 261, and earlier references therein. (d) Adrian, H.; Bailey, P. D.; Rees, D. C.; Wightman, R. H. J. Chem. Soc., Chem. Commun. 1998, 2251. (e) Faitg, T.; Soulie, J.; Lallemand J.-Y.; Ricard, L. Tetrahedron: Asymmetry 1999, 2165. (f) Hall, A.; Bailey, P. D.; Rees, D. C.; Rosair, G. M.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 2000, 329.
    • (2000) J. Chem. Soc., Perkin Trans. 1 , pp. 329
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    • note
    • For additional examples of preparation of conduramine synthons, see refs 4 and 9b.
  • 32
  • 33
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    • Stereoselective preparation of epoxides can be achieved by the aid of the structure of the substrates, especially in the cyclic systems. The presence of a hydroxyl group close to the olefinic bond strongly determines the epoxide stereochemistry. For studies of the directive effect of the hydroxyl group, see: (a) Henbest, H. B. Proc. Chem. Soc. 1963, 159. (b) Chamberlain, P.; Roberts, M. L.; Whitham, G. H. J. Chem. Soc., B 1970, 1374. (c) Prat, D.; Delpech, B.; Lett, R. Tetrahedron Lett. 1986, 27, 711.
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  • 34
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    • Stereoselective preparation of epoxides can be achieved by the aid of the structure of the substrates, especially in the cyclic systems. The presence of a hydroxyl group close to the olefinic bond strongly determines the epoxide stereochemistry. For studies of the directive effect of the hydroxyl group, see: (a) Henbest, H. B. Proc. Chem. Soc. 1963, 159. (b) Chamberlain, P.; Roberts, M. L.; Whitham, G. H. J. Chem. Soc., B 1970, 1374. (c) Prat, D.; Delpech, B.; Lett, R. Tetrahedron Lett. 1986, 27, 711.
    • (1970) J. Chem. Soc. B. , pp. 1374
    • Chamberlain, P.1    Roberts, M.L.2    Whitham, G.H.3
  • 35
    • 85022253152 scopus 로고
    • Stereoselective preparation of epoxides can be achieved by the aid of the structure of the substrates, especially in the cyclic systems. The presence of a hydroxyl group close to the olefinic bond strongly determines the epoxide stereochemistry. For studies of the directive effect of the hydroxyl group, see: (a) Henbest, H. B. Proc. Chem. Soc. 1963, 159. (b) Chamberlain, P.; Roberts, M. L.; Whitham, G. H. J. Chem. Soc., B 1970, 1374. (c) Prat, D.; Delpech, B.; Lett, R. Tetrahedron Lett. 1986, 27, 711.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 711
    • Prat, D.1    Delpech, B.2    Lett, R.3
  • 37
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    • note
    • 2, 25°C, 86% yield (three steps)
  • 38
    • 2142755400 scopus 로고    scopus 로고
    • note
    • 2 at 25°C afforded the corresponding piperonyl bromide 6b in 96% yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.