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Volumn 10, Issue 11, 2008, Pages 2323-2326

A cascade palladium-mediated cross-coupling/electrocyclization approach to the construction of fused Bi- and tricyclic rings

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EID: 56349086054     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8007952     Document Type: Article
Times cited : (39)

References (49)
  • 5
    • 0003995267 scopus 로고    scopus 로고
    • Negishi, E.-I, Ed, John Wiley and Sons, Inc, New York, Section IV
    • (b) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., Ed.; John Wiley and Sons, Inc.: New York, 2002; Vol. 1, Section IV.
    • (2002) Handbook of Organopalladium Chemistry for Organic Synthesis , vol.1
  • 8
    • 0001064425 scopus 로고    scopus 로고
    • Selected examples of carbopalladation/Stille coupling:(a) Burns, B.; Grigg, R.; Ratananukul, P.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron Lett. 1988, 29, 5565.
    • Selected examples of carbopalladation/Stille coupling:(a) Burns, B.; Grigg, R.; Ratananukul, P.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron Lett. 1988, 29, 5565.
  • 12
    • 0034665354 scopus 로고    scopus 로고
    • Fretwell, P.; Grigg, R.; Sansano, J. M.; Sridharan, V.; Sukirthalingam, S; Wilson, D; Redpath, J. Tetrahedron 2000, 56, 7525. See also refs 8 and 9.
    • (e) Fretwell, P.; Grigg, R.; Sansano, J. M.; Sridharan, V.; Sukirthalingam, S; Wilson, D; Redpath, J. Tetrahedron 2000, 56, 7525. See also refs 8 and 9.
  • 13
    • 0008845915 scopus 로고    scopus 로고
    • Selected carbopalladations terminating with other cross-coupling manifolds; see ref 2a and: (a) Zhang, Y, Negishi, E.-I. J. Am. Chem. Soc. 1989, 111, 3454
    • Selected carbopalladations terminating with other cross-coupling manifolds; see ref 2a and: (a) Zhang, Y.; Negishi, E.-I. J. Am. Chem. Soc. 1989, 111, 3454.
  • 23
    • 0027077907 scopus 로고    scopus 로고
    • de Meijere has focused mainly on fully intramolecular variants:(a) Meyer, F. E.; Henniges, H.; de Meijere, A. Tetrahedron Lett. 1992, 33, 8039.
    • de Meijere has focused mainly on fully intramolecular variants:(a) Meyer, F. E.; Henniges, H.; de Meijere, A. Tetrahedron Lett. 1992, 33, 8039.
  • 27
    • 0035903689 scopus 로고    scopus 로고
    • For a stepwise construction of the electrocyclization substrate, see: e
    • For a stepwise construction of the electrocyclization substrate, see: (e) von Zezschwitz, P.; Petry, F.; de Meijere, A. Chem. Eur. J. 2001, 7, 4035.
    • (2001) Chem. Eur. J , vol.7 , pp. 4035
    • von Zezschwitz, P.1    Petry, F.2    de Meijere, A.3
  • 28
    • 0035814397 scopus 로고    scopus 로고
    • Suffert has mainly studied specific 4- and 5-exo-dig cyclizations; for leading references, see: (a) Suffert, J.; Salem, B.; Klotz, P. J. Am. Chem. Soc. 2001, 123, 12107.
    • Suffert has mainly studied specific 4- and 5-exo-dig cyclizations; for leading references, see: (a) Suffert, J.; Salem, B.; Klotz, P. J. Am. Chem. Soc. 2001, 123, 12107.
  • 34
    • 42149191168 scopus 로고    scopus 로고
    • For an outstanding recent application to fenestrane synthesis, see: g
    • For an outstanding recent application to fenestrane synthesis, see: (g) Hulot, C.; Blond, G.; Suffert, J. J. Am. Chem. Soc. 2008, 130, 5046.
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 5046
    • Hulot, C.1    Blond, G.2    Suffert, J.3
  • 38
    • 30744456247 scopus 로고    scopus 로고
    • For a review of cross-coupling/electrocylization in synthesis, see: k
    • For a review of cross-coupling/electrocylization in synthesis, see: (k) Beaudry, C. M.; Malerich, J. P.; Trauner, D. Chem. Rev. 2005, 105, 4757.
    • (2005) Chem. Rev , vol.105 , pp. 4757
    • Beaudry, C.M.1    Malerich, J.P.2    Trauner, D.3
  • 39
    • 59849096784 scopus 로고    scopus 로고
    • See the Supporting Information for details of substrate preparation and proof of stereochemistry
    • See the Supporting Information for details of substrate preparation and proof of stereochemistry.
  • 45
    • 3543046453 scopus 로고
    • For an example of fused-ring cyclooctatrienes that do not undergo 6π-electrocyclization, see: a
    • For an example of fused-ring cyclooctatrienes that do not undergo 6π-electrocyclization, see: (a) Paquette, L. A.; Photis, J. M.; Micheli, R. P. J. Am. Chem. Soc. 1977, 99, 7899.
    • (1977) J. Am. Chem. Soc , vol.99 , pp. 7899
    • Paquette, L.A.1    Photis, J.M.2    Micheli, R.P.3
  • 47
    • 0141520554 scopus 로고    scopus 로고
    • Varela, J. A.; Castedo, L.; Saá, C. Org. Lett. 2003, 5, 2841. See also ref 10.
    • (c) Varela, J. A.; Castedo, L.; Saá, C. Org. Lett. 2003, 5, 2841. See also ref 10.
  • 49
    • 28744447770 scopus 로고    scopus 로고
    • For a single previous instance of a presumed 8π/aromatization-driven 6π-cyclization, see: Pelly, S. C, Parkinson, C. J, van Otterlo, W. A. L, de Koning, C. B. J. Org. Chem. 2005, 70, 10474. While this work was in progress, an elegant synthesis of fenestranes via 8π/6π-cyclization was reported by Suffert; see ref 6f
    • For a single previous instance of a presumed 8π/aromatization-driven 6π-cyclization, see: Pelly, S. C.; Parkinson, C. J.; van Otterlo, W. A. L.; de Koning, C. B. J. Org. Chem. 2005, 70, 10474. While this work was in progress, an elegant synthesis of fenestranes via 8π/6π-cyclization was reported by Suffert; see ref 6f.


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