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Volumn 44, Issue 31, 2005, Pages 4944-4948

A concise and general method for doubly attaching 2-ketosugars to aglycon diols: Synthesis of the gomphosides and spectinomycin

Author keywords

Fused ring systems; Glycosylation; Gomphosides; Natural products; Spectinomycin

Indexed keywords

ALCOHOLS; ANTIBIOTICS; BACTERIA; COMPLEXATION; DERIVATIVES; KETONES; SYNTHESIS (CHEMICAL);

EID: 23744476405     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200500434     Document Type: Article
Times cited : (21)

References (41)
  • 11
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    • For a pertinent review on spectinomycin, see: W. Rosenbrook, Jr., J. Antibiot. 1979, 32, S211-S227.
    • (1979) J. Antibiot. , vol.32
    • Rosenbrook Jr., W.1
  • 16
    • 0012265825 scopus 로고    scopus 로고
    • (Eds.: B. Ernst, G. W. Hart, P. Sinaÿ), Wiley-VCH, Weinheim
    • c) V. Pozgay in Carbohydrates in Chemistry and Biology, Part I (Eds.: B. Ernst, G. W. Hart, P. Sinaÿ), Wiley-VCH, Weinheim, 2000, pp. 332-336.
    • (2000) Carbohydrates in Chemistry and Biology, Part I , pp. 332-336
    • Pozgay, V.1
  • 17
    • 0035861619 scopus 로고    scopus 로고
    • For recent applications towards β-D-mannosides, see: d) M. Nitz, D. R. Bundle, J. Org. Chem. 2001, 66, 8411-8423;
    • (2001) J. Org. Chem. , vol.66 , pp. 8411-8423
    • Nitz, M.1    Bundle, D.R.2
  • 25
    • 33645198473 scopus 로고    scopus 로고
    • See ref. [9] (footnote 19 therein)
    • c) See ref. [9] (footnote 19 therein).
  • 28
    • 33645200720 scopus 로고    scopus 로고
    • note
    • The alternative possibility, cyclo-hemiketalization of 13 by OH→C=O attack from the upper (equatorial) face would lead to the sterically and thermodynamically unfavorable trans-transoid-trans-fused product in which the central dioxane ring is forced into a boat (or twist-boat) conformation.
  • 29
    • 0022479554 scopus 로고
    • Racemic 16, in noncrystalline form, has previously been prepared through elaboration of the pyranoid portion through an aldehyde/diene cycloaddition approach: S. Danishefsky, J. Aubé, M. Bednarski, J. Am. Chem. Soc. 1986, 108, 4145-4149.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 4145-4149
    • Danishefsky, S.1    Aubé, J.2    Bednarski, M.3
  • 30
    • 0016647353 scopus 로고
    • Gomphogenin (17) was prepared from digitoxin by hydrolytic removal of the sugars and conversion of its aglycon, digitoxigenin, through a known seven-step procedure: Y. Kamano, G. R. Pettit, M. Tozawa, J. Chem. Soc. Perkin Trans. 1 1975, 1972-1976;
    • (1975) J. Chem. Soc. Perkin Trans. 1 , pp. 1972-1976
    • Kamano, Y.1    Pettit, G.R.2    Tozawa, M.3
  • 32
    • 0016689897 scopus 로고
    • The catalyst was adapted from the Ru/C-mediated hydrogenation of spectinomycin (7), which provided an epimeric mixture mainly consisting of the (4R)-dihydro analogue 8: W. Rosenbrook, Jr., R. E. Carney, J. Antibiot. 1975, 28, 953-959.
    • (1975) J. Antibiot. , vol.28 , pp. 953-959
    • Rosenbrook Jr., W.1    Carney, R.E.2
  • 35
    • 33645203454 scopus 로고    scopus 로고
    • note
    • 2, which accounts for the comparatively large difference in melting behavior.
  • 39
    • 33645197684 scopus 로고    scopus 로고
    • note
    • The less reactive ulosyl bromide (11) gave complex mixtures under these conditions which contained substantial amounts of 21.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.