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Volumn 3, Issue 10, 2005, Pages 2031-2036

Synthesis of a 4,5-epoxy-2-cyclohexen-1-one derivative via epoxide ring opening, 1,3-carbonyl transposition and epoxide ring regeneration: A synthetic study on a scyphostatin analogue

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; HYDROPHILICITY; MOLECULAR STRUCTURE; REDUCTION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 19944369147     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b504039f     Document Type: Article
Times cited : (23)

References (51)
  • 16
    • 0034278620 scopus 로고    scopus 로고
    • Synthetic studies on the hydrophilic moiety of scyphostatin 1: (a) M. K. Gurjar and S. Hotha, Heterocycles, 2000, 53, 1885;
    • (2000) Heterocycles , vol.53 , pp. 1885
    • Gurjar, M.K.1    Hotha, S.2
  • 21
    • 0041350398 scopus 로고    scopus 로고
    • Synthetic studies on the Hydrophobic moiety of scyphostatin 1
    • (f) L. M. Murray, P. O'Brien and R. J. K. Taylor, Org. Lett., 2003, 5, 1943. Synthetic studies on the Hydrophobic moiety of scyphostatin 1:;
    • (2003) Org. Lett. , vol.5 , pp. 1943
    • Murray, L.M.1    O'Brien, P.2    Taylor, R.J.K.3
  • 22
    • 0034682135 scopus 로고    scopus 로고
    • (g) T. R. Hoye and M. A. Tennakoon, Org. Lett., 2000, 2, 1481. Synthetic studies on scyphostatin analogue:;
    • (2000) Org. Lett. , vol.2 , pp. 1481
    • Hoye, T.R.1    Tennakoon, M.A.2
  • 32
    • 19944396077 scopus 로고    scopus 로고
    • note
    • 1H NMR NOE experiments. A tentative explanation for the reversal in the facial selectivity of the epoxidation of the Diels-Alder adducts is that while the methylene group of the spiro-lactone ring placed at a pseudo-axial position of the enone ring in the transition state for 3a, it is placed at a pseudo-equatrial position in the case of 3b to avoid repulsion between the CbzNH group and the reagent;
  • 33
    • 19944405692 scopus 로고    scopus 로고
    • 6: C, 66.83; H, 5.35; N, 3.54%. Found: C, 66.71; H, 5.55; N, 3.48%
    • 6: C, 66.83; H, 5.35; N, 3.54%. Found: C, 66.71; H, 5.55; N, 3.48%;
  • 34
    • 19944418724 scopus 로고    scopus 로고
    • 6: C, 66.83; H, 5.35: N, 3.54%. Found: C, 66.87; H, 5.34; N, 3.54%
    • 6: C, 66.83; H, 5.35: N, 3.54%. Found: C, 66.87; H, 5.34; N, 3.54%.
  • 41
    • 19944403823 scopus 로고    scopus 로고
    • The numbering system of 5 was based on that of 4
    • The numbering system of 5 was based on that of 4.
  • 50
    • 19944363071 scopus 로고    scopus 로고
    • Bromination at the C4 position via enolization of 18 with LDA also failed
    • Bromination at the C4 position via enolization of 18 with LDA also failed.
  • 51
    • 19944396709 scopus 로고    scopus 로고
    • The calculations were performed with PC Spartan Pro, Wavefunction, Inc., Irvine, CA 92715
    • The calculations were performed with PC Spartan Pro, Wavefunction, Inc., Irvine, CA 92715.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.