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Volumn 68, Issue 11, 2003, Pages 4195-4205

A tandem metal carbene cyclization-cycloaddition approach to the pseudolaric acids

Author keywords

[No Author keywords available]

Indexed keywords

PSEUDOLARIC ACIDS;

EID: 0038441588     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026399m     Document Type: Article
Times cited : (62)

References (69)
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    • Ph.D. Dissertation, University of Mississippi, MS
    • (a) Bonk, J. D. Ph.D. Dissertation, University of Mississippi, MS, 1997.
    • (1997)
    • Bonk, J.D.1
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    • Examples of carbene cyclization intramolecular cycloaddition: (a) McMills, M. C.; Zhuang L.; Wright, D. L. Watt, W. Tetrahedron Lett. 1994, 35, 8311. (b) Dauben, W. G.; Dinges, J.; Smith, T. C. J. Org. Chem. 1993, 58, 7635.
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  • 27
    • 0027724867 scopus 로고
    • Examples of carbene cyclization intramolecular cycloaddition: (a) McMills, M. C.; Zhuang L.; Wright, D. L. Watt, W. Tetrahedron Lett. 1994, 35, 8311. (b) Dauben, W. G.; Dinges, J.; Smith, T. C. J. Org. Chem. 1993, 58, 7635.
    • (1993) J. Org. Chem. , vol.58 , pp. 7635
    • Dauben, W.G.1    Dinges, J.2    Smith, T.C.3
  • 28
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    • Examples of carbene cyclization intermolecular cycloaddition. Illudins and ptaquilosins: (a) Padwa, A.; Sandanayaka, V. P.; Curtis, E. A. J. Am. Chem. Soc. 1994, 116, 2667. (b) Padwa, A.; Curtis, E. A.; Sandanayaka, V. P. J. Org. Chem. 1996, 61, 73. Zaragozic acids: (c) Koyama, H.; Ball, R. G.; Berger, G. D. Tetrahedron Lett. 1994, 35, 9185. (d) Hodgson, D. M.; Bailey, J. M.; Harrison, T. Tetrahedron Lett. 1996, 37, 4623. Brevicomin: (e) Padwa, A.; Fryxell, G. E. Zhi, L. J. Am. Chem. Soc. 1990. 112, 3100.
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    • Padwa, A.1    Sandanayaka, V.P.2    Curtis, E.A.3
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    • Examples of carbene cyclization intermolecular cycloaddition. Illudins and ptaquilosins: (a) Padwa, A.; Sandanayaka, V. P.; Curtis, E. A. J. Am. Chem. Soc. 1994, 116, 2667. (b) Padwa, A.; Curtis, E. A.; Sandanayaka, V. P. J. Org. Chem. 1996, 61, 73. Zaragozic acids: (c) Koyama, H.; Ball, R. G.; Berger, G. D. Tetrahedron Lett. 1994, 35, 9185. (d) Hodgson, D. M.; Bailey, J. M.; Harrison, T. Tetrahedron Lett. 1996, 37, 4623. Brevicomin: (e) Padwa, A.; Fryxell, G. E. Zhi, L. J. Am. Chem. Soc. 1990. 112, 3100.
    • (1996) J. Org. Chem. , vol.61 , pp. 73
    • Padwa, A.1    Curtis, E.A.2    Sandanayaka, V.P.3
  • 30
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    • Examples of carbene cyclization intermolecular cycloaddition. Illudins and ptaquilosins: (a) Padwa, A.; Sandanayaka, V. P.; Curtis, E. A. J. Am. Chem. Soc. 1994, 116, 2667. (b) Padwa, A.; Curtis, E. A.; Sandanayaka, V. P. J. Org. Chem. 1996, 61, 73. Zaragozic acids: (c) Koyama, H.; Ball, R. G.; Berger, G. D. Tetrahedron Lett. 1994, 35, 9185. (d) Hodgson, D. M.; Bailey, J. M.; Harrison, T. Tetrahedron Lett. 1996, 37, 4623. Brevicomin: (e) Padwa, A.; Fryxell, G. E. Zhi, L. J. Am. Chem. Soc. 1990. 112, 3100.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 9185
    • Koyama, H.1    Ball, R.G.2    Berger, G.D.3
  • 31
    • 0030600124 scopus 로고    scopus 로고
    • Examples of carbene cyclization intermolecular cycloaddition. Illudins and ptaquilosins: (a) Padwa, A.; Sandanayaka, V. P.; Curtis, E. A. J. Am. Chem. Soc. 1994, 116, 2667. (b) Padwa, A.; Curtis, E. A.; Sandanayaka, V. P. J. Org. Chem. 1996, 61, 73. Zaragozic acids: (c) Koyama, H.; Ball, R. G.; Berger, G. D. Tetrahedron Lett. 1994, 35, 9185. (d) Hodgson, D. M.; Bailey, J. M.; Harrison, T. Tetrahedron Lett. 1996, 37, 4623. Brevicomin: (e) Padwa, A.; Fryxell, G. E. Zhi, L. J. Am. Chem. Soc. 1990. 112, 3100.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 4623
    • Hodgson, D.M.1    Bailey, J.M.2    Harrison, T.3
  • 32
    • 0025108625 scopus 로고
    • Examples of carbene cyclization intermolecular cycloaddition. Illudins and ptaquilosins: (a) Padwa, A.; Sandanayaka, V. P.; Curtis, E. A. J. Am. Chem. Soc. 1994, 116, 2667. (b) Padwa, A.; Curtis, E. A.; Sandanayaka, V. P. J. Org. Chem. 1996, 61, 73. Zaragozic acids: (c) Koyama, H.; Ball, R. G.; Berger, G. D. Tetrahedron Lett. 1994, 35, 9185. (d) Hodgson, D. M.; Bailey, J. M.; Harrison, T. Tetrahedron Lett. 1996, 37, 4623. Brevicomin: (e) Padwa, A.; Fryxell, G. E. Zhi, L. J. Am. Chem. Soc. 1990. 112, 3100.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 3100
    • Padwa, A.1    Fryxell, G.E.2    Zhi, L.3
  • 34
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    • There is one example of a cycloaddition of an isomünchnone with a propargyl ether: Maier, M. E.; Schoffling, B. Chem. Ber. 1989, 122, 1081.
    • (1989) Chem. Ber. , vol.122 , pp. 1081
    • Maier, M.E.1    Schoffling, B.2
  • 63
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    • Although the stereochemistry of 31 was not rigorously established, it was presumed to be the α-alcohol on the basis of the characteristic reactivity patterns of oxabicyclic compounds; see: Chiu, P.; Lautens, M. Top. Curr. Chem. 1997, 190, 1.
    • (1997) Top. Curr. Chem. , vol.190 , pp. 1
    • Chiu, P.1    Lautens, M.2


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