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Volumn 63, Issue 48, 2007, Pages 11878-11885

Convenient synthetic route to a dehydrorotenoid via selective intramolecular aldol condensation of 1,2-diaryl diketone

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; BENZOFURAN DERIVATIVE; DEHYDROROTENOID; KETONE DERIVATIVE; NATURAL PRODUCT; PYRAN DERIVATIVE; RUTHENIUM; UNCLASSIFIED DRUG;

EID: 35348843387     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.09.032     Document Type: Article
Times cited : (32)

References (34)
  • 24
    • 35348914069 scopus 로고    scopus 로고
    • 4 is generated in situ from ruthenium(III) chloride, see:
  • 27
    • 0000204205 scopus 로고
    • The yield of diketone increased when pH was controlled to reduce the corresponding cleavage reaction of 1,2-diketone compound, see:
    • The yield of diketone increased when pH was controlled to reduce the corresponding cleavage reaction of 1,2-diketone compound, see:. Lee D.G., and Chang V.S. J. Org. Chem. 44 (1979) 2726
    • (1979) J. Org. Chem. , vol.44 , pp. 2726
    • Lee, D.G.1    Chang, V.S.2
  • 28
    • 0037134880 scopus 로고    scopus 로고
    • Modifying the experimental conditions with l-proline-induced intramolecular aldol reaction in good yields because compound 14 contains acidic proton at C-2 which can be easily eliminated to give the conjugated carbonyl as side product, see:
    • Modifying the experimental conditions with l-proline-induced intramolecular aldol reaction in good yields because compound 14 contains acidic proton at C-2 which can be easily eliminated to give the conjugated carbonyl as side product, see:. Northrup A.B., and MacMillan D.W. J. Am. Chem. Soc. 124 (2002) 6798
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 6798
    • Northrup, A.B.1    MacMillan, D.W.2
  • 29
    • 35348913452 scopus 로고    scopus 로고
    • note
    • 2=0.2788 for 9714 reflections [I>2σ(I)]; temp=293(2) K; the crystal structure for 19 has been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 641936.
  • 30
    • 35348827658 scopus 로고    scopus 로고
    • note
    • Products 14 and 17 display optical activity, presumably as a function of employing l-proline for the aldol cyclization. We were unable to assign the absolute stereochemistry of the major enantiomer.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.