100909-95-3Relevant academic research and scientific papers
Total Synthesis of Catunaregin and Preliminary Evaluation of Its Antitumor Activity
Abe, Hideki,Hikichi, Takuma,Emori, Kosuke,Yokosuka, Akihito,Mimaki, Yoshihiro,Kobayashi, Toyoharu,Ito, Hisanaka
, p. 1655 - 1664 (2018)
The total synthesis of catunaregin in both racemic and optically active forms was accomplished. The enantioselective synthesis uses the Evans aldol strategy, with an oxazolidinone or thiazolidinethione as the chiral auxiliary. The key features include a syn-selective aldol reaction to form the Evans-syn or non-Evans-syn product, and a successive ketalization reaction of a furanyl diol derivative under acidic conditions. The biological properties of the synthetic racemate and both enantiomers were evaluated against A549 and HL-60 human cancer cells.
Synthesis of tri- and tetrasubstituted furans catalyzed by trifluoroacetic acid
Stauffer, Frederic,Neier, Reinhard
, p. 3535 - 3537 (2007/10/03)
(matrix presented) Substituted 2-hydroxy-3-acetylfurans are synthesized by alkylation of tert-butyl acetoacetate with an α-haloketone followed by treatment of the obtained intermediate with trifluoroacetic acid (TFA). A second alkylation of the intermedia
Michael Adducts of a Half-Blocked Enedione as Sources of 3-Substituted 2,5-Diketones and 2,5-Dialkylfurans
Mackay, Donald,Neeland, Edward G.,Taylor, Nicholas J.
, p. 2351 - 2361 (2007/10/02)
The dioxazolylbutenones 2a, formed by isomerization of the Diels-Alder adducts of 2,5-dimethylfuran with (nitrosocarbonyl)benzene , are efficient Michael acceptors of a wide variety of carbon and heteroatom nucleophiles.The resulting adducts 5 function as half-blocked 1,4-diones.They can be converted into the corresponding diketones 10 by hot aqueous EtOH or Pd-H2 or into the 3-substituted 2,5-dimethylfurans 19 by BF3, either directly or by way of 10.Hydroperoxide anion adds conjugatively to 2a to give the epoxide 23, but 1,2-addition is competitive and is followed by dioxazole ring opening to give a peroxy compound regarded as 21.The cycloaddition of 2,5-dialkylfurans and nitrosocompounds is general, but 2-methylfuran appears to add (although in poor yield) in the opposite mode, the adduct spontaneously isomerizing to the mono-O-benzoyloximino enedione 32.
