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Volumn 10, Issue 23, 2008, Pages 5417-5420

A diastereoselective total synthesis of trans-trikentrin A: A ring contraction approach

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; INDOLE ALKALOID; TRIKENTRIN A;

EID: 61349193156     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8023105     Document Type: Article
Times cited : (45)

References (50)
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    • For selected reviews, see: a
    • For selected reviews, see: (a) Higuchi, K.; Kawasaki, T. Nat. Prod. Rep. 2007, 24, 843.
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    • Higuchi, K.1    Kawasaki, T.2
  • 2
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    • and references therein
    • (b) Gul, W.; Hamann, M. T. Life Sci. 2005, 78, 442, and references therein.
    • (2005) Life Sci , vol.78 , pp. 442
    • Gul, W.1    Hamann, M.T.2
  • 6
    • 33847007723 scopus 로고    scopus 로고
    • Syntheses of cis-trikentrins and of herbindoles: (a) Jackson, S. K.; Kerr, M. A. J. Org. Chem. 2007, 72, 1405.
    • Syntheses of cis-trikentrins and of herbindoles: (a) Jackson, S. K.; Kerr, M. A. J. Org. Chem. 2007, 72, 1405.
  • 20
    • 0000987191 scopus 로고    scopus 로고
    • Syntheses of trans-trikentrins: MacLeod, J. K.; Ward, A.; Willis, A. C. Aust. J. Chem. 1998, 51, 177 and refs 4f,g,i,j,k, and m.
    • Syntheses of trans-trikentrins: MacLeod, J. K.; Ward, A.; Willis, A. C. Aust. J. Chem. 1998, 51, 177 and refs 4f,g,i,j,k, and m.
  • 21
    • 0043159086 scopus 로고
    • For reviews concerning ring contraction reactions, see: a, Hart, H, Karabastos, G. J, Eds, Academic Press: New York and London
    • For reviews concerning ring contraction reactions, see: (a) Redmore, D.; Gutsche, C. D. In Advances in Alicyclic Chemistry; Hart, H., Karabastos, G. J., Eds.; Academic Press: New York and London, 1971; Vol. 3, p 1.
    • (1971) Advances in Alicyclic Chemistry , vol.3 , pp. 1
    • Redmore, D.1    Gutsche, C.D.2
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    • For a review concerning Tl(III)-mediated ring contractions, see: (c) Ferraz, H. M. C.; Silva, L. F., Jr. Quim. Nova 2000, 23, 216.
    • For a review concerning Tl(III)-mediated ring contractions, see: (c) Ferraz, H. M. C.; Silva, L. F., Jr. Quim. Nova 2000, 23, 216.
  • 26
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    • For Tl(III)-mediated ring contraction in the synthesis of alkaloids, see: (d) Rigby, J. H.; Pigge, F. C. J. Org. Chem. 1995, 60, 7392.
    • For Tl(III)-mediated ring contraction in the synthesis of alkaloids, see: (d) Rigby, J. H.; Pigge, F. C. J. Org. Chem. 1995, 60, 7392.
  • 27
    • 61349136797 scopus 로고    scopus 로고
    • See also references cited in reviews 6b and 7c.
    • (e) See also references cited in reviews 6b and 7c.
  • 36
    • 0000837348 scopus 로고    scopus 로고
    • 4, see: Hutchins, R. O.; Kandasamy, D.; Dux, F., III; Maryanoff, C. A.; Rotstein, D.; Goldsmith. B.; Burgoyne, W.; Cistone, F.; Dalessandro, J.; Puglis, J. J. Org. Chem. 1978, 43, 2259.
    • 4, see: Hutchins, R. O.; Kandasamy, D.; Dux, F., III; Maryanoff, C. A.; Rotstein, D.; Goldsmith. B.; Burgoyne, W.; Cistone, F.; Dalessandro, J.; Puglis, J. J. Org. Chem. 1978, 43, 2259.
  • 40
    • 61349201321 scopus 로고    scopus 로고
    • The product of this reaction was also obtained by an alternative route. See Supporting Information for details
    • The product of this reaction was also obtained by an alternative route. See Supporting Information for details.
  • 42
    • 61349117218 scopus 로고    scopus 로고
    • 7a,b,8
    • 7a,b,8
  • 43
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    • 3/ anisole. see: Wada, Y.; Nagasaki, H.; Tokuda, M.; Orito, K. J. Org. Chem. 2007, 72, 2008.
    • 3/ anisole. see: Wada, Y.; Nagasaki, H.; Tokuda, M.; Orito, K. J. Org. Chem. 2007, 72, 2008.
  • 44
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    • All attempts to obtain the ester 6 with a Boc group instead of the Bn failed in the Heck reaction.
    • All attempts to obtain the ester 6 with a Boc group instead of the Bn failed in the Heck reaction.
  • 45
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    • 4, see: (a) Passacantilli, P. Tetrahedron Lett. 1989, 30, 5349.
    • 4, see: (a) Passacantilli, P. Tetrahedron Lett. 1989, 30, 5349.
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    • 1H NMR analysis.
    • 1H NMR analysis.
  • 48
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    • For stereoselective syntheses of indane 20, see: (a) 20b (30:1, trans: cis) Arp, F. O.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 10482.
    • For stereoselective syntheses of indane 20, see: (a) 20b (30:1, trans: cis) Arp, F. O.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 10482.
  • 49
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    • 20a (12:1, cis:trans) Bailey, W. F.; Mealy, M. J.; Wiberg, K. B. Org. Lett. 2002, 4, 791.
    • (b) 20a (12:1, cis:trans) Bailey, W. F.; Mealy, M. J.; Wiberg, K. B. Org. Lett. 2002, 4, 791.


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