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Volumn 128, Issue 8, 2006, Pages 2594-2603

Evolution of a strategy for the synthesis of structurally complex batzelladine alkaloids. Enantioselective total synthesis of the proposed structure of batzelladine F and structural revision

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN; MASS SPECTROMETERS; NITROGEN; SAPONIFICATION; SYNTHESIS (CHEMICAL);

EID: 33644658317     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0574320     Document Type: Article
Times cited : (49)

References (50)
  • 4
    • 23944434392 scopus 로고    scopus 로고
    • (a) For reviews summarizing the isolation, structure and synthesis of batzelladine alkaloids, see: Berlinck, R. G. S.; Kossuga, M. H. J. Nat. Prod. 2005, 22, 516-550 and earlier reviews in this series,
    • (2005) J. Nat. Prod. , vol.22 , pp. 516-550
    • Berlinck, R.G.S.1    Kossuga, M.H.2
  • 9
    • 33644636424 scopus 로고    scopus 로고
    • note
    • These data were not presented in the paper or the Supporting Information.
  • 12
    • 0035980339 scopus 로고    scopus 로고
    • (a) Our synthesis of the natural product has been outlined: Cohen, F.; Overman, L. E. J. Am. Chem. Soc. 2001, 123, 10782-10783.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 10782-10783
    • Cohen, F.1    Overman, L.E.2
  • 20
    • 0019408557 scopus 로고
    • Without this basic additive, the bis-dimethyl acetal was isolated in quantitative yield. See: Woodward, R. B. et al. J. Am. Chem. Soc. 1981, 103, 3210-3213.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 3210-3213
    • Woodward, R.B.1
  • 27
    • 0033525676 scopus 로고    scopus 로고
    • Stereoselection in the tethered Biginelli condensation has been thoroughly investigated: McDonald, A. I.; Overman, L. E. J. Org. Chem. 1999, 64, 1520-1528.
    • (1999) J. Org. Chem. , vol.64 , pp. 1520-1528
    • McDonald, A.I.1    Overman, L.E.2
  • 29
    • 33644648846 scopus 로고    scopus 로고
    • note
    • A model compound similar to 26 bearing a methyl ester was completely resistant to both basic and acidic hydrolysis.
  • 32
    • 33644644389 scopus 로고    scopus 로고
    • note
    • Synthesized from unsaturated azido benzoate 15 in a fashion analogous to 29; see Supporting Information.
  • 43
    • 33644658289 scopus 로고    scopus 로고
    • note
    • These reactions were conducted on a small scale (<1 mg) and analyzed by HPLC-MS.
  • 45
    • 33644646041 scopus 로고    scopus 로고
    • note
    • Molecular mechanics modeling shows that the ester group of intermediates of this type exists preferentially in a conformation in which the methine hydrogen and the carbonyl π-system are nearly orthogonal. This feature is likely responsible for the failure to generate the ester enolate of 69.
  • 46
    • 33644662313 scopus 로고    scopus 로고
    • note
    • 3SiH, TFA) either failed to reduce 71 or led to decomposition.
  • 47
    • 33644637301 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum of 76 corresponding to the left-hand tricyclic portion were nearly identical to that of 68. The two most diagnostic peaks were the vinyl methyl singlet at δ 2.26 and the allylic methine at δ 4.25 (dd, J = 11.7, 5.2 Hz). Both of these resonances were absent from the spectrum of 75, and were replaced with an allylic methine at δ 4.49 (q, J = 6.3 Hz) and a multiplet at δ 2.45-2.30 corresponding to the allylic methylene.
  • 48
    • 33644647579 scopus 로고    scopus 로고
    • note
    • Details are provided in the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.