71589-55-4Relevant articles and documents
Comparative studies of palladium and copper-catalysed γ-arylation of silyloxy furans with diaryliodonium salts
Alexander, Taylor S.,Clay, Travis J.,Maldonado, Bryan,Nguyen, Johny M.,Martin, David B.C.
, p. 2229 - 2238 (2019/03/06)
The γ-arylation of substituted silyl-activated butenolides has been studied using a broad scope of unsymmetrical hypervalent diaryliodonium salts via a palladium- or copper-catalysed coupling reaction, yielding interesting reactivity trends. The mild catalytic conditions and coupling partner variability provide access to synthetically useful building blocks toward the pursuit of aryl-lactone containing natural products and allows for facile diversification.
Synthesis and cytotoxic activity of γ-aryl substituted α-alkylidene-γ-lactones and α-alkylidene-γ-lactams
Albrecht, Anna,Koszuk, Jacek F.,Modranka, Jakub,Rozalski, Marek,Krajewska, Urszula,Janecka, Anna,Studzian, Kazimierz,Janecki, Tomasz
, p. 4872 - 4882 (2008/12/23)
A series of 5-aryl-3-alkylidenedihydrofuran-2(3H)-ones 6a-g″ and 11a,b as well as 5-aryl-3-methylidenepyrrolidin-2-ones 10a-c and 12 were synthesized starting from 4-aryl-2-diethoxyphosphoryl-4-oxobutanoates 3a-g. Reaction sequence includes reduction or reductive amination of the carbonyl group, lactonization or lactamization step and finally the Horner-Wadsworth-Emmons olefination of aldehydes using thus obtained 5-aryl-3-diethoxyphosphoryl-3,4-dihydrofuran-2(5H)-ones 5a-g″ or 5-aryl-3-diethoxyphosphorylpyrrolidin-2-ones 9a-c. Furanones 6 and 11, as well as pyrrolidinones 10 and 12, were evaluated in vitro against mouse leukemia cell line L-1210 and two human leukemia cell lines HL-60 and NALM-6. Several of the obtained furanones proved to be very potent against all three cell lines with IC50 values lower than 6 μM. Structure-activity relationships of these compounds, as well as 5-alkyl or 5-arylmethyl-3-methylidenedihydrofuran-2(3H)-ones 13a-e, previously obtained in our laboratory, are discussed.
