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Volumn 40, Issue 23, 1999, Pages 4445-4448

Chiral, densely functionalized cycloheptanes from carbohydrates. I. The nitrone route

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL GROUP; BENZYL DERIVATIVE; CARBOHYDRATE DERIVATIVE; CYCLOHEPTANE DERIVATIVE; FREE RADICAL; NITRO DERIVATIVE;

EID: 0033523035     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00769-8     Document Type: Article
Times cited : (31)

References (31)
  • 11
    • 0013593696 scopus 로고    scopus 로고
    • note
    • Unpublished results from this laboratory (manuscript in preparation). The 7-exo-trig free radical cyclization of acyclic precursors from sugars leading to chiral cycloheptanes is unprecedented.
  • 13
    • 0000582924 scopus 로고
    • Intramolecular 1,3-dipolar cycloaddition
    • Trost, B. M.; Fleming, I.; Semmelhack, M. F., Eds.; Pergamon Press, Oxford, Chapter 4.10
    • For a review on nitrone cycloadditions, see: Wade, P. A. Intramolecular 1,3-dipolar cycloaddition; in Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I.; Semmelhack, M. F., Eds.; Pergamon Press, Oxford, 1991; Vol 4, Chapter 4.10, pp 1111.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 1111
    • Wade, P.A.1
  • 14
    • 0000118768 scopus 로고    scopus 로고
    • The intramolecular nitrone cycloaddition has been extensively analyzed and documented in sugar templates. For leading references: (a)
    • The intramolecular nitrone cycloaddition has been extensively analyzed and documented in sugar templates. For leading references: (a) Torrente, S.; Noya, B.; Paredes, M. D.; Alonso, R. J. Org. Chem. 1997, 62, 6710;
    • (1997) J. Org. Chem. , vol.62 , pp. 6710
    • Torrente, S.1    Noya, B.2    Paredes, M.D.3    Alonso, R.4
  • 25
    • 0013619754 scopus 로고    scopus 로고
    • All new compounds showed excellent analytical and spectroscopic data
    • All new compounds showed excellent analytical and spectroscopic data.
  • 26
    • 0013620160 scopus 로고    scopus 로고
    • note
    • 2O/4:1, 0.2 M, 55 °C) to improve the yields of compounds 4 and 5 for the synthesis of the advanced intermediates 10 and 15, in order to compare their respective reactivity in the 1,3-DC reaction.
  • 27
    • 0013565635 scopus 로고    scopus 로고
    • note
    • The 60% yield in the synthesis of compound 7 from 6 was not optimized. In this reaction other more polar (probably mono and/or disubstituted methylated derivatives) were detected, but not isolated.
  • 28
    • 0013566089 scopus 로고    scopus 로고
    • note
    • 2O]. This product was dissolved in chlorobenzene (3 mL) and refluxed (bath at 130 °C) for 20 h. The solvent was removed and the residue was submitted to chromatography (hexane: ethyl acetate, 1:3) to give adduct 16 (16 mg, 50%) as an oil.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.