메뉴 건너뛰기




Volumn 67, Issue 52, 2011, Pages 10097-10104

Lessons learned while traversing the welwitindolinone alkaloids obstacle course

Author keywords

Aromatic Cope rearrangement; Chlorination; O Acylation; Vilsmeier Haack reaction; Welwitindolinones

Indexed keywords

ALKALOID DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG; WELWITINDOLINONE ALKALOID DERIVATIVE;

EID: 82255162600     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.09.088     Document Type: Article
Times cited : (27)

References (60)
  • 29
    • 80053493129 scopus 로고    scopus 로고
    • While the present manuscript was under review for publication, a report appeared in J. Am. Chem. Soc., ASAP on the total synthesis of welwitindolinone C(2)
    • For the synthesis of welwitindolinone D (3), see Ref. 1b.: While the present manuscript was under review for publication, a report appeared in J. Am. Chem. Soc., ASAP on the total synthesis of welwitindolinone C(2): A.D. Huters, K.W. Quasdorf, E.D. Styduhar, and N.K. Garg J. Am. Chem. Soc. 133 2011 15797 15799
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 15797-15799
    • Huters, A.D.1    Quasdorf, K.W.2    Styduhar, E.D.3    Garg, N.K.4
  • 30
    • 0001354153 scopus 로고
    • For a review on the Vilsmeier-Haack reaction, see
    • For a review on the Vilsmeier-Haack reaction, see: O. Meth-Con, and S.P. Stanforth Comp. Org. Syn. 2 1991 777 794
    • (1991) Comp. Org. Syn. , vol.2 , pp. 777-794
    • Meth-Con, O.1    Stanforth, S.P.2
  • 31
    • 0027420791 scopus 로고
    • For an example of deconjugative methylation of a cyclic enal, see
    • For an example of deconjugative methylation of a cyclic enal, see: R.H. Burnell, C. Côté, and N. Théberge J. Nat. Prod. 56 1993 1459 1467
    • (1993) J. Nat. Prod. , vol.56 , pp. 1459-1467
    • Burnell, R.H.1    Côté, C.2    Théberge, N.3
  • 32
    • 0007682030 scopus 로고    scopus 로고
    • TFEF=2,2,2-trifluoroethylformate
    • TFEF=2,2,2-trifluoroethylformate G.H. Zayia Org. Lett. 1 1999 989 991
    • (1999) Org. Lett. , vol.1 , pp. 989-991
    • Zayia, G.H.1
  • 34
    • 0000110916 scopus 로고
    • See Supplementary data for synthesis.: Funk and co-workers have also reported difficulties with a similar acylation step. See: Ref. 3i.: For a full discussion of this observation, see Ref. 1d.: H.J. Reich J. Org. Chem. 39 1974 428 429
    • (1974) J. Org. Chem. , vol.39 , pp. 428-429
    • Reich, H.J.1
  • 49
    • 0002075454 scopus 로고
    • For a review on the Cope rearrangement, see
    • For a review on the Cope rearrangement, see: S.J. Rhoads, and N.R. Raulins Org. React. 22 1975 1 252
    • (1975) Org. React. , vol.22 , pp. 1-252
    • Rhoads, S.J.1    Raulins, N.R.2
  • 59
    • 33646547703 scopus 로고    scopus 로고
    • For a review, see: N. Krause, A.S.K. Hashmi, Wiley-VCH Weinheim
    • For a review, see: M. Ogasawara, and T. Hayashi N. Krause, A.S.K. Hashmi, Modern Allene Chemistry Vol. 1 2004 Wiley-VCH Weinheim 93 140
    • (2004) Modern Allene Chemistry , vol.1 , pp. 93-140
    • Ogasawara, M.1    Hayashi, T.2
  • 60
    • 0442267595 scopus 로고
    • This axiom is a variation of Woodward's pithy statement: "...there are no general reactions." See: W.O. Milligan, Organic Synthesis Huston, TX
    • This axiom is a variation of Woodward's pithy statement: "...there are no general reactions." See: R.B. Woodward W.O. Milligan, Proceedings of the Robert A. Welch Foundation Conference on Chemical Research, XII Organic Synthesis 1969 3 6 Huston, TX
    • (1969) Proceedings of the Robert A. Welch Foundation Conference on Chemical Research, XII , pp. 3-6
    • Woodward, R.B.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.