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Volumn 11, Issue 11, 2009, Pages 2393-2396

Concise synthesis of capuramycin

Author keywords

[No Author keywords available]

Indexed keywords

AMINOGLYCOSIDE; CAPURAMYCIN; TUBERCULOSTATIC AGENT;

EID: 66149190559     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900458w     Document Type: Article
Times cited : (45)

References (53)
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    • DOTS (directly observed therapy shortcourse therapy) uses a battery of drugs in a prescribed order to eradicate tuberculosis and avoid the creation of drug-resistant strains of the disease
    • DOTS (directly observed therapy shortcourse therapy) uses a battery of drugs in a prescribed order to eradicate tuberculosis and avoid the creation of drug-resistant strains of the disease.
  • 6
    • 19744367767 scopus 로고    scopus 로고
    • Cohen, J. Science 2004, 306, 1872.
    • (2004) Science , vol.306 , pp. 1872
    • Cohen, J.1
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    • 66149185339 scopus 로고    scopus 로고
    • Uncharacterizable byproducts were isolated in addition to the overdeacetylation products
    • Uncharacterizable byproducts were isolated in addition to the overdeacetylation products.
  • 31
    • 0037449629 scopus 로고    scopus 로고
    • and references therein
    • North, M. Tetrahedron: Asymmetry 2003, 14, 147, and references therein.
    • (2003) Tetrahedron: Asymmetry , vol.14 , pp. 147
    • North, M.1
  • 34
    • 66149185340 scopus 로고    scopus 로고
    • The stereochemistry of 5a was established by the advanced Mosher method, see Supporting Information.
    • The stereochemistry of 5a was established by the advanced Mosher method, see Supporting Information.
  • 35
    • 9244244705 scopus 로고    scopus 로고
    • Ti(OiPr)4 is known to form Ti-oxo species such as [Ti7O4](OR)20, [Ti8O6](OR)20, and [Ti12O16](OR)16 with trace amount of water through Ti(OiPr)3(OH), see: Hubert-Pfalzgraf, L. G. J. Mater. Chem. 2004, 14, 3113.
    • Ti(OiPr)4 is known to form Ti-oxo species such as [Ti7O4](OR)20, [Ti8O6](OR)20, and [Ti12O16](OR)16 with trace amount of water through Ti(OiPr)3(OH), see: Hubert-Pfalzgraf, L. G. J. Mater. Chem. 2004, 14, 3113.
  • 38
    • 66149190594 scopus 로고    scopus 로고
    • We are currently investigating a chiral reagent which promotes the reaction of 4 to 5a with high yield and high selectivity
    • We are currently investigating a chiral reagent which promotes the reaction of 4 to 5a with high yield and high selectivity.
  • 39
    • 66149164358 scopus 로고    scopus 로고
    • Addition of pyridine was indispensable for successful inversion of the C5′-stereocenter of 5b with ClCH2CO2H.
    • Addition of pyridine was indispensable for successful inversion of the C5′-stereocenter of 5b with ClCH2CO2H.
  • 42
    • 66149176838 scopus 로고    scopus 로고
    • The orthoester 7 shows a characteristic chemical shift of 1.78 ppm (CH3) in the 1H NMR spectrum.
    • The orthoester 7 shows a characteristic chemical shift of 1.78 ppm (CH3) in the 1H NMR spectrum.
  • 43
    • 66149160284 scopus 로고    scopus 로고
    • Due to the fact that all triflate ion associated glycosylations with 6(entries 1-3) yielded a mixture of R-and-mannosides, the mannosyl carbenium ion generated directly from 6 or through the orthoester 7 would be transformed to the R-glycosyl triflate which furnishes the undesired-mannoside 8b.
    • Due to the fact that all triflate ion associated glycosylations with 6(entries 1-3) yielded a mixture of R-and-mannosides, the mannosyl carbenium ion generated directly from 6 or through the orthoester 7 would be transformed to the R-glycosyl triflate which furnishes the undesired-mannoside 8b.
  • 44
    • 0022626632 scopus 로고    scopus 로고
    • The formation of orthoesters had previously been reported with a number of different glycosyl donors which react through an oxonium ion intermediate and contain a C2-acetyl group, see: Harreus, A. H, Kunz, H. Liebigs Ann. Chem 1986, 717
    • The formation of orthoesters had previously been reported with a number of different glycosyl donors which react through an oxonium ion intermediate and contain a C2-acetyl group, see: Harreus, A. H.; Kunz, H. Liebigs Ann. Chem 1986, 717.
  • 47
    • 33947468159 scopus 로고    scopus 로고
    • Winstein, S.; Clippinger, E.; Fainberg, A. H.; Heck, R.; , G. C.; Robinson, G. C. J. Am. Chem. Soc. 1956, 78, 328.
    • Winstein, S.; Clippinger, E.; Fainberg, A. H.; Heck, R.; , G. C.; Robinson, G. C. J. Am. Chem. Soc. 1956, 78, 328.
  • 48
    • 84868945306 scopus 로고    scopus 로고
    • The isolated orthoester 7 could be rearranged to 8a by the treatment with HBF4·OEt2 compex in CH2Cl2.
    • The isolated orthoester 7 could be rearranged to 8a by the treatment with HBF4·OEt2 compex in CH2Cl2.
  • 50
    • 84868936849 scopus 로고    scopus 로고
    • Deprotection of the BOM-protected 13 under these conditions was ∼40% yield.
    • Deprotection of the BOM-protected 13 under these conditions was ∼40% yield.
  • 53
    • 66149162992 scopus 로고    scopus 로고
    • See Supporting Informataion
    • See Supporting Informataion.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.