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Volumn , Issue 3, 2009, Pages 412-422

[4+2]/HyBRedOx approach to C-naphthyl glycosides: Failure in the projuglone series and reinvestigation of the HyBRedOx sequence

Author keywords

Cycloaddition; Dienophiles; Glycosides; Heterocycles; Tin

Indexed keywords


EID: 58649107376     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800655     Document Type: Article
Times cited : (6)

References (37)
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    • for an elegant synthesis of Vineomycinone B2 via the formation of a C ring by a Bradsher-type [4+2]-heterocycloaddition, see: V. Bollitt, C. Mioskowski, R. O. Kollah, S. Manna, D. Rajapaksa, J. R. Falck, J. Am. Chem. Soc. 2001, 123, 6937-6938.
    • c) for an elegant synthesis of Vineomycinone B2 via the formation of a C ring by a Bradsher-type [4+2]-heterocycloaddition, see: V. Bollitt, C. Mioskowski, R. O. Kollah, S. Manna, D. Rajapaksa, J. R. Falck, J. Am. Chem. Soc. 2001, 123, 6937-6938.
  • 18
    • 58649093787 scopus 로고    scopus 로고
    • For a relevant approach to C-glycosylanthraquinone based on a 1,3-dipolar cycloaddition, see: F. M. Hausser, X. Hu, Org. Lett. 2002, 4, 977-978.
    • For a relevant approach to C-glycosylanthraquinone based on a 1,3-dipolar cycloaddition, see: F. M. Hausser, X. Hu, Org. Lett. 2002, 4, 977-978.
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    • H. Uno, J. Org. Chem. 1986, 51, 350-358.
    • (1986) J. Org. Chem , vol.51 , pp. 350-358
    • Uno, H.1
  • 25
    • 58649121334 scopus 로고    scopus 로고
    • The correct NMR analysis of compound 12 requires the use of deuterated chloroform stabilized on silver.
    • The correct NMR analysis of compound 12 requires the use of deuterated chloroform stabilized on silver.
  • 29
    • 58649085309 scopus 로고    scopus 로고
    • In this paper, adducts have been designed as endo or exo, whatever the mechanism concerted or not, For SnCl4-catalyzed reactions, a nonconcerted mechanism is presumed
    • 4-catalyzed reactions, a nonconcerted mechanism is presumed.
  • 30
    • 58649110464 scopus 로고    scopus 로고
    • Global efficiency in the formation of adduct 14c appeared to be very dependent on the quality of the tin chloride used. Thus, yields can be severely limited by acid-catalyzed hydrolysis of enol ether 8, which produces a ketone that is barely separable from the adduct exo- 14c
    • Global efficiency in the formation of adduct 14c appeared to be very dependent on the quality of the tin chloride used. Thus, yields can be severely limited by acid-catalyzed hydrolysis of enol ether 8, which produces a ketone that is barely separable from the adduct exo- 14c.
  • 31
    • 58649120864 scopus 로고    scopus 로고
    • 4-promoted cycloreversion of 14b at room temperature cannot be totally excluded.
    • 4-promoted cycloreversion of 14b at room temperature cannot be totally excluded.
  • 32
    • 58649098001 scopus 로고    scopus 로고
    • Spartan, Wavefunction Inc., Irvine, CA 92612, U.S.A.
    • Spartan, Wavefunction Inc., Irvine, CA 92612, U.S.A.
  • 36
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    • 3 could be a more appropriate reagent for oxidation under the milder conditions of the putative borane.
    • 3 could be a more appropriate reagent for oxidation under the milder conditions of the putative borane.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.