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Volumn 12, Issue 7, 2010, Pages 1580-1583

Concise total syntheses of aspalathin and nothofagin

Author keywords

[No Author keywords available]

Indexed keywords

ASPALATHIN; BIOLOGICAL PRODUCT; CHALCONE DERIVATIVE; NOTHOFAGIN;

EID: 77950240519     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100315g     Document Type: Article
Times cited : (26)

References (31)
  • 10
    • 77950208746 scopus 로고    scopus 로고
    • 2O, Pyr).
    • 2O, Pyr).
  • 11
    • 77950196287 scopus 로고    scopus 로고
    • 3 (5 equiv) in. DMF at 80 °C for 1 h.
    • 3 (5 equiv) in. DMF at 80 °C for 1 h.
  • 14
    • 0037467849 scopus 로고    scopus 로고
    • 1H NMR analysis of the individual a and β Cl anomers of dipivaloate 4a.
    • 1H NMR analysis of the individual a and β Cl anomers of dipivaloate 4a.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 907
    • Rani, S.1    Vankar, Y.D.2
  • 15
    • 77950210659 scopus 로고    scopus 로고
    • Attempts to achieve greater conversions in the C-glycosylation reactions by adding excess Lewis acid (>10 equiv), by elevating the reaction temperature (*25 °C), or by increasing the reaction time (>lh) only led to lower overall yields of 5, presumably due to acid-induced cleavage of the aromatic benzyl ether protecting groups.
    • Attempts to achieve greater conversions in the C-glycosylation reactions by adding excess Lewis acid (>10 equiv), by elevating the reaction temperature (*25 °C), or by increasing the reaction time (>lh) only led to lower overall yields of 5, presumably due to acid-induced cleavage of the aromatic benzyl ether protecting groups.
  • 17
    • 77950262792 scopus 로고    scopus 로고
    • Prepared in the same manner as 4a, except with the substitution of isobutryl chloride for pivaloyl chloride in the esteriflcaton step
    • (a) Prepared in the same manner as 4a, except with the substitution of isobutryl chloride for pivaloyl chloride in the esteriflcaton step
  • 18
    • 77950277171 scopus 로고    scopus 로고
    • Prepared in the same manner as 4a, except with the substitution of cyclohexyl carbonyl chloride for pivaloyl chloride in the esteriflcaton. step.
    • (b) Prepared in the same manner as 4a, except with the substitution of cyclohexyl carbonyl chloride for pivaloyl chloride in the esteriflcaton. step.
  • 25
    • 77950241091 scopus 로고    scopus 로고
    • Glycoside 5b could also be used in the Vilsmeier formylation reaction, providing an 83% yield of the corresponding isobutyryl-protected aryl aldehyde. This substrate was not chosen to advance through the remainder of the synthesis for two reasons; first, the cost of isobutyryl chloride required for the preparation of 4b (and thus 5b) is about twice that of pivaloyl chloride, and second, slightly lower overall yields (∼55%) were obtained when the isobutyryl-protected aryl aldehyde was subjected to the coupling (with lithiated 10a and 10b) and isobutyrate deprotection reactions.
    • Glycoside 5b could also be used in the Vilsmeier formylation reaction, providing an 83% yield of the corresponding isobutyryl-protected aryl aldehyde. This substrate was not chosen to advance through the remainder of the synthesis for two reasons; first, the cost of isobutyryl chloride required for the preparation of 4b (and thus 5b) is about twice that of pivaloyl chloride, and second, slightly lower overall yields (∼55%) were obtained when the isobutyryl-protected aryl aldehyde was subjected to the coupling (with lithiated 10a and 10b) and isobutyrate deprotection reactions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.