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Volumn 3, Issue 18, 2001, Pages 2919-2922

C-glycosides to fused polycyclic ethers. An efficient entry into the A-D ring system of Gambierol

Author keywords

[No Author keywords available]

Indexed keywords

CIGUATOXIN; ETHER DERIVATIVE; GAMBIEROL; GLYCOSIDE; POLYCYCLIC HYDROCARBON;

EID: 0035818014     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016434w     Document Type: Article
Times cited : (70)

References (44)
  • 11
    • 0042722937 scopus 로고    scopus 로고
    • Sasaki and Yamamoto have employed somewhat circuitous routes to the similarly substituted gambierol F,G-ring system. See refs 3d and 4
    • Sasaki and Yamamoto have employed somewhat circuitous routes to the similarly substituted gambierol F,G-ring system. See refs 3d and 4.
  • 17
    • 0043224163 scopus 로고    scopus 로고
    • The analogous cycloaddition reaction between Danishersky's diene and 2 proceeds in 95% ee and 65% yield. See ref 8
    • The analogous cycloaddition reaction between Danishersky's diene and 2 proceeds in 95% ee and 65% yield. See ref 8.
  • 18
    • 0042221850 scopus 로고    scopus 로고
    • 3
    • 3.
  • 20
    • 0041721533 scopus 로고    scopus 로고
    • Compound 4 is enantiomeric to that expected on the basis of Jacobsen's results. See ref 13
    • Compound 4 is enantiomeric to that expected on the basis of Jacobsen's results. See ref 13.
  • 21
    • 0042722935 scopus 로고    scopus 로고
    • The enantiomeric excess of 4 was determined using a chiracel OD HPLC column
    • The enantiomeric excess of 4 was determined using a chiracel OD HPLC column.
  • 36
    • 0042221848 scopus 로고    scopus 로고
    • The use of propenylmagnesium chloride resulted in the selective formation of the undesired β-C-allyl glycoside, whereas the use of triallyl aluminum and triallyl borane resulted in the formation of 1.5:1 and 1:1.5 mixtures of α-and β-C-allyl glycosides, respectively
    • The use of propenylmagnesium chloride resulted in the selective formation of the undesired β-C-allyl glycoside, whereas the use of triallyl aluminum and triallyl borane resulted in the formation of 1.5:1 and 1:1.5 mixtures of α-and β-C-allyl glycosides, respectively.
  • 38
    • 0043224162 scopus 로고    scopus 로고
    • Determined from NOE experiments. See Supporting Information
    • Determined from NOE experiments. See Supporting Information
  • 39
    • 0033618291 scopus 로고    scopus 로고
    • To the best of our knowledge, this is the first example of this reaction. For related Claisen rearrangements to C-glycosides, see: (a) Vidal, T.; Haudrechy, A.; Langlois, Y. Tetrahedron Lett. 1999, 40, 5677.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 5677
    • Vidal, T.1    Haudrechy, A.2    Langlois, Y.3
  • 42
    • 2142858450 scopus 로고
    • The relative stereochemistry was established through the use of extensive NOE experiments. The absolute stereochemistry was established through the conversion of 13 into the corresponding C-6 Mosher's esters and using the Kakisawa method for determining the absolute stereochemistry. See ref 2 and Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 4092
    • Ohtani, I.1    Kusumi, T.2    Kashman, Y.3    Kakisawa, H.4
  • 43
    • 0003942864 scopus 로고
    • Wiley: New York
    • 4 reduction of the C-10 ketone is expected on the basis of axial attack on the ketone and from the side opposite the C-7 angular methyl group. For a discussion of related reductions in cyclohexanones, see: Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley: New York, 1994; pp 734-735.
    • (1994) Stereochemistry of Organic Compounds , pp. 734-735
    • Eliel, E.L.1    Wilen, S.H.2    Mander, L.N.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.