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Volumn 54, Issue 22, 1998, Pages 5883-5892

Samarium diiodide-induced radical cyclization of oxime ether connected with formyl group: Synthesis of 4-pyrimidinyl- and 4-purinylpyrrolidin-3-ol nucleoside analogues

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE DERIVATIVE; OXIME; PYRIMIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; SAMARIUM;

EID: 0032575233     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00274-9     Document Type: Article
Times cited : (55)

References (40)
  • 9
    • 0002543904 scopus 로고    scopus 로고
    • 4. For recent examples of the radical reaction of oxime ethers, see: a) Clive, D. L. J.; Zhang, J. Chem. Commun. 1997, 549-550.
    • (1997) Chem. Commun. , pp. 549-550
    • Clive, D.L.J.1    Zhang, J.2
  • 19
    • 4243481130 scopus 로고
    • U. S. Patent 3920772, 1975
    • 6. Stach, L. J. U. S. Patent 3920772, 1975 (Chem. Abstr. 1976, 84, 89603d).
    • (1976) Chem. Abstr. , vol.84
    • Stach, L.J.1
  • 20
    • 0003882087 scopus 로고
    • Patai, S., Ed., John Wiley & Sons: New York
    • 1H-NMR spectroscopy. In general, the downfield shifts of signals due to the imino hydrogen of the E-oxime ether are observed by the influence of the neighboring alkoxy group on the oxime ether moiety. See: McCarty, C. G. The Chemistry of Functional Groups; The chemistry of the carbon-nitrogen double bond; Patai, S., Ed., John Wiley & Sons: New York, 1970; pp.383-392.
    • (1970) The Chemistry of Functional Groups; the Chemistry of the Carbon-Nitrogen Double Bond , pp. 383-392
    • McCarty, C.G.1
  • 21
    • 0010647180 scopus 로고    scopus 로고
    • note
    • 8. The stannyl radical-induced radical cyclization of 4 gave a 3:1 mixture of trans-5 and cis-5 in 66% combined yield.
  • 24
    • 0010729818 scopus 로고    scopus 로고
    • note
    • 10. We have observed no remarkable effect of the geometry of the starting oxime ether group on either the chemical yield or trans/cis selectivity of radical cyclization product.
  • 25
    • 0010646535 scopus 로고    scopus 로고
    • note
    • 2, was found to be crucial for successful seven-membered ring formation. See: reference 3c.
  • 28
    • 0000335222 scopus 로고
    • 13. For reviews, see: a) Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745-1768.
    • (1992) Chem. Rev. , vol.92 , pp. 1745-1768
    • Huryn, D.M.1    Okabe, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.