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Volumn 72, Issue 26, 2007, Pages 9936-9946

Development of a highly β-selective ribosylation reaction without using neighboring group participation: Total synthesis of (+)-caprazol, a core structure of caprazamycins

Author keywords

[No Author keywords available]

Indexed keywords

AMINOHYDROXYLATION; INTRAMOLECULAR REDUCTIVE AMINATION; RIBOSYLATION REACTION;

EID: 37549058458     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701699h     Document Type: Article
Times cited : (81)

References (85)
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    • (c) Takeuchi, T.; Igarashi, M.; Naganawa, H.; Hamada, M. JP 2003012687, 2001.
  • 14
    • 37549050796 scopus 로고    scopus 로고
    • Ochi, K.; Ezaki, M.; Morita, I.; Komori, T.; Kohsaka, M. ER 0333177, 1989, A2.
    • (a) Ochi, K.; Ezaki, M.; Morita, I.; Komori, T.; Kohsaka, M. ER 0333177, 1989, A2.
  • 35
    • 37549017017 scopus 로고    scopus 로고
    • Introduction of a uracil by the Vorbruggen method following construction of ribosyl diazepanone was reported to have some drawbacks. See ref. 7a
    • Introduction of a uracil by the Vorbruggen method following construction of ribosyl diazepanone was reported to have some drawbacks. See ref. 7a.
  • 55
    • 37549022515 scopus 로고    scopus 로고
    • Preparation of donors can be found in the Supporting Information
    • Preparation of donors can be found in the Supporting Information.
  • 60
    • 37549048846 scopus 로고    scopus 로고
    • 1H NMR spectrum.
    • 1H NMR spectrum.
  • 68
    • 4243553426 scopus 로고    scopus 로고
    • (a) Becke, A. D. Phys. Rev. 1998, 38, 3098-3100.
    • (1998) Phys. Rev , vol.38 , pp. 3098-3100
    • Becke, A.D.1
  • 69
    • 0001174959 scopus 로고    scopus 로고
    • (b) Becke, A. D. Phys. Rev. 1998, 37, 785-789.
    • (1998) Phys. Rev , vol.37 , pp. 785-789
    • Becke, A.D.1
  • 78
    • 37549041191 scopus 로고    scopus 로고
    • Initial attempts to construct the diazepanone via deprotection of the Cbz group in a model compound such as A followed by reductive amination of the aldehyde, both promoted by catalytic hydrogenation with Pd/C, were unsuccessful because of difficulty in hydrogenating the corresponding cyclic imine. Additional forcing conditions under medium pressure gave a 5,6-dihydrouridine derivative B due to over-reduction Chemical Equation Presented
    • Initial attempts to construct the diazepanone via deprotection of the Cbz group in a model compound such as A followed by reductive amination of the aldehyde, both promoted by catalytic hydrogenation with Pd/C, were unsuccessful because of difficulty in hydrogenating the corresponding cyclic imine. Additional forcing conditions under medium pressure gave a 5,6-dihydrouridine derivative B due to over-reduction (Chemical Equation Presented)
  • 83
    • 0037424037 scopus 로고    scopus 로고
    • Desilylation during Pd-catalyzed hydrogenation reactions was reported. See
    • Desilylation during Pd-catalyzed hydrogenation reactions was reported. See: Sajiki, H.; Ikawa, T.; Hattori, K.; Hirota, K. Chem. Commun. 2003, 654-655.
    • (2003) Chem. Commun , pp. 654-655
    • Sajiki, H.1    Ikawa, T.2    Hattori, K.3    Hirota, K.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.