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Volumn 125, Issue 40, 2003, Pages 12080-12081

Identification of a novel Michael acceptor group for the reversible addition of oxygen- and sulfur-based nucleophiles. Synthesis and reactivity of the 3-alkylidene-3H-indole 1-oxide function of Avrainvillamide

Author keywords

[No Author keywords available]

Indexed keywords

3H INDOLE 1 OXIDE DERIVATIVE; AMIDE; AVRAINVILLAMIDE; INDOLE DERIVATIVE; NATURAL PRODUCT; NUCLEOPHILE DERIVATIVE; OXYGEN DERIVATIVE; STEPHACIDIN A; SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0141992728     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0372006     Document Type: Article
Times cited : (61)

References (23)
  • 3
    • 0141916287 scopus 로고    scopus 로고
    • Avrainvillamide, a Cytotoxic Marine Natural Product, and the Derivatives thereof. U.S. Patent 6,066,635, 2000
    • Isolation of avrainvillamide: (a) Fenical, W.; Jensen, P.; Cheng, X. C. Avrainvillamide, a Cytotoxic Marine Natural Product, and the Derivatives thereof. U.S. Patent 6,066,635, 2000.
    • Fenical, W.1    Jensen, P.2    Cheng, X.C.3
  • 6
    • 0042812136 scopus 로고    scopus 로고
    • (d) An alternative sequence of formation of bonds a and b was recently proposed for the biosynthesis of 2 from 1, contemporous with and independent of the present work: Nussbaum, F. Angew. Chem., Int. Ed. 2003, 42, 3068.
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 3068
    • Nussbaum, F.1
  • 16
    • 0038106171 scopus 로고    scopus 로고
    • For discussion of 1,3-addition of nucleophiles to nitrones, see: (a) Bloch, R. Chem. Rev. 1998, 98, 1407.
    • (1998) Chem. Rev. , vol.98 , pp. 1407
    • Bloch, R.1
  • 18
    • 0001852305 scopus 로고    scopus 로고
    • Rate determined by inversion-transfer, analyzed with the CIFIT program: Bain, A. D.; Kramer, J. A. J. Magn. Reson. 1996, 118a, 21.
    • (1996) J. Magn. Reson. , vol.118 A , pp. 21
    • Bain, A.D.1    Kramer, J.A.2
  • 19
    • 0141916285 scopus 로고    scopus 로고
    • note
    • 1-D NOESY experiments confirmed the stereochemistry of the exocyclic double bond to be that shown.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.