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Volumn 44, Issue 12, 2005, Pages 1854-1856

Total synthesis of caprazol, a core structure of the caprazamycin antituberculosis antibiotics

Author keywords

[No Author keywords available]

Indexed keywords

SYNTHESIS (CHEMICAL);

EID: 17044432700     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462439     Document Type: Article
Times cited : (104)

References (35)
  • 17
    • 17044378609 scopus 로고    scopus 로고
    • note
    • [5a]
  • 18
    • 0033544402 scopus 로고    scopus 로고
    • During the course of our synthetic studies on nucleoside antibiotics, it was revealed that the introduction of a protecting group or substituent on this type of alcohol was quite difficult: S. Ichikawa, S. Shuto, M. Matsuda, J. Am. Chem. Soc. 1999, 121, 10270-10280.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 10270-10280
    • Ichikawa, S.1    Shuto, S.2    Matsuda, M.3
  • 23
    • 0025790925 scopus 로고
    • The stereochemistry of the 5′ position of 5 was determined to be the R configuration by the modified Mosher method with the amide derivatives, which were prepared by deprotection of the Cbz protecting group of 5 and subsequent acylation of the liberated amine with 2-methoxy-2- trifluoromethylphenylacetic acid (see the Supporting Information); T. Kusumi, T. Fukushima, I. Ohtani, H. Kakisawa, Tetrahedron Lett. 1991, 32, 2939-2942.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 2939-2942
    • Kusumi, T.1    Fukushima, T.2    Ohtani, I.3    Kakisawa, H.4
  • 24
    • 17044405521 scopus 로고    scopus 로고
    • note
    • Details for the preparation and characterization may be found in the Supporting Information.
  • 27
    • 17044401011 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum.
  • 29
    • 17044375930 scopus 로고    scopus 로고
    • note
    • 3, N,N-dimethylformamide).
  • 31
    • 17044397334 scopus 로고    scopus 로고
    • note
    • It was presumed that the methyl source was the formaldehyde generated upon cleavage of the BOM protecting group from the 3 position.
  • 35
    • 13244292401 scopus 로고    scopus 로고
    • S. Hikishima, N. Minakawa, K. Kuramoto, Y. Fujisawa, M. Ogawa, A. Matsuda, Angew. Chem. 2005, 117, 602-604; Angew. Chem. Int. Ed. 2005, 44, 596-598.
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 596-598


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.