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Volumn 72, Issue 10, 2007, Pages 3972-3975

Total synthesis of marine sponge bis(indole) alkaloids of the topsentin class

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; ESTERS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 34248595120     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070286r     Document Type: Article
Times cited : (46)

References (39)
  • 8
    • 5744247694 scopus 로고    scopus 로고
    • For a review on marine bis(indole) alkaloids, see:, and references cited therein
    • For a review on marine bis(indole) alkaloids, see: Yang, C.-G.; Huang, H.; Jiang, B. Curr. Org. Chem. 2004, 8, 1691 and references cited therein.
    • (2004) Curr. Org. Chem , vol.8 , pp. 1691
    • Yang, C.-G.1    Huang, H.2    Jiang, B.3
  • 9
    • 0001469756 scopus 로고    scopus 로고
    • For the first isolation of topsentins 1a-c, see: Bartik, K.; Braekman, J.-C.; Daloze, D.; Stoller, C.; Huysecom, J.; Vandevyver, G.; Ottinger, R. Can. J. Chem. 1987, 65, 2118.
    • (a) For the first isolation of topsentins 1a-c, see: Bartik, K.; Braekman, J.-C.; Daloze, D.; Stoller, C.; Huysecom, J.; Vandevyver, G.; Ottinger, R. Can. J. Chem. 1987, 65, 2118.
  • 10
    • 0032900672 scopus 로고    scopus 로고
    • See also ref 6b therein for the isolation of topsentins 1a and 1c. (b) For isolation of isobromodeoxytopsentin 1d, see: Shin, J.; Seo, Y.; Cho, K. W.; Rho, J.-R.; Sim, C. J. J. Nat. Prod. 1999, 62, 647.
    • See also ref 6b therein for the isolation of topsentins 1a and 1c. (b) For isolation of isobromodeoxytopsentin 1d, see: Shin, J.; Seo, Y.; Cho, K. W.; Rho, J.-R.; Sim, C. J. J. Nat. Prod. 1999, 62, 647.
  • 11
    • 84941834949 scopus 로고    scopus 로고
    • For isolation of topsentin D 2a, see: Braekman, J. C.; Daloze, D.; Moussiaux, B.; Stoller, C.; Deneubourg, F. Pure Appl. Chem. 1989, 61, 509.
    • (c) For isolation of topsentin D 2a, see: Braekman, J. C.; Daloze, D.; Moussiaux, B.; Stoller, C.; Deneubourg, F. Pure Appl. Chem. 1989, 61, 509.
  • 12
    • 33847082059 scopus 로고    scopus 로고
    • For isolation of (+)-spongotine B 2b, see: Bao, B.; Sun, Q.; Yao, X.; Hong, J.; Lee. C.-O.; Cho, H. Y.; Jung, J. H. J. Nat. Prod. 2007, 70, 2.
    • (d) For isolation of (+)-spongotine B 2b, see: Bao, B.; Sun, Q.; Yao, X.; Hong, J.; Lee. C.-O.; Cho, H. Y.; Jung, J. H. J. Nat. Prod. 2007, 70, 2.
  • 13
    • 34248508896 scopus 로고
    • For patent literature, see: a, Eur. Patent 272 810, 129417q
    • For patent literature, see: (a) Gunasekera, S. P.; Cross, S. S.; Kashman Y.; Lui M. S. Eur. Patent 272 810, 1988; Chem. Abstr. 1988, 109, 129417q.
    • (1988) Chem. Abstr , vol.109
    • Gunasekera, S.P.1    Cross, S.S.2    Kashman, Y.3    Lui, M.S.4
  • 14
  • 15
    • 34248513574 scopus 로고    scopus 로고
    • Gunasekera, S. P.; Cross, S. S.; Kashman, Y.; Lui, M. S.; Rinehart, K. L.; Tsujii, S. U.S. Patent 4 866 084, 1989; Chem. Abstr. 1990, 112, 185775d.
    • (c) Gunasekera, S. P.; Cross, S. S.; Kashman, Y.; Lui, M. S.; Rinehart, K. L.; Tsujii, S. U.S. Patent 4 866 084, 1989; Chem. Abstr. 1990, 112, 185775d.
  • 28
    • 11444267769 scopus 로고    scopus 로고
    • The β-amino indolic N-hydroxylamine 5 has been prepared in a two-step sequence from N-(tert-butoxycarbonyl)- aminoacetaldehyde in 84% overall yield. This aldehyde is commercially available. However, for a recent and efficient synthesis of this compound, see: Myers, M. C.; Pokorski, J. K.; Apella, D. H. Org. Lett. 2004, 6, 4699.
    • The β-amino indolic N-hydroxylamine 5 has been prepared in a two-step sequence from N-(tert-butoxycarbonyl)- aminoacetaldehyde in 84% overall yield. This aldehyde is commercially available. However, for a recent and efficient synthesis of this compound, see: Myers, M. C.; Pokorski, J. K.; Apella, D. H. Org. Lett. 2004, 6, 4699.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.