69556-75-8Relevant academic research and scientific papers
Efficient syntheses of thiono and dithio analogues of tetronic acid
Labruere, Raphael,Desbene-Finck, Stephanie,Helissey, Philippe,Giorgi-Renault, Sylviane
, p. 4163 - 4166 (2006)
Thiono and dithio lactone analogues of 4-hydroxyfuran2(5H)-one (tetronic acid) were synthesized in three steps from tetronic acid and thiolotetronic acid. Their usefulness in pharmacomodulation were exemplified by the synthesis of thio analogues of 4-aza-
REGIOSPECIFIC O-ALKYLATION OF Β-TETRONIC ACIDS UNDER MITSUNOBU REACTION CONDITIONS
Bajwa, Joginder S.,Anderson, Robert C.
, p. 6973 - 6976 (1990)
An improved procedure for regiospecific O-alkylation of β-tetronic acids with primary and secondary alcohols, based upon Mitsunobu conditions, is presented.The reaction conditions are very mild and compatible with a variety of hydroxyl protecting groups such as MOM, t-BuMe2Si, isopropylidine and esters.
Total synthesis of (-)-2-methoxy-2-butenolide-3-cinnamate and its antimicrobial potentials
Dastager, Syed G.,Gajbhiye, Jayant,Khan, AbuJunaid,Kumar, Pradeep,Nayak, Rashmi,Sahu, Amit Kumar,Said, Madhukar S.,Udavant, Rohini
, p. 1 - 6 (2020)
The first total synthesis of (-)-2-methoxy-2-butenolide-3-cinnamate (butenolide cinnamate) was achieved using commercially available starting material. The synthesized compound was found to have promising antibacterial activity against Gram-negative strai
Lewis Acid Mediated Addition of Indoles and Alcohols to Tetronic Acid and Tetramic Acids
Banales Mejia, Fernando,Lafferty, Megan M.,Melvin, Sophia J.,Truax, Nathanyal J.,Kean, Maeve H.,Pelkey, Erin T.
supporting information, p. 260 - 264 (2017/01/25)
The electrophilic substitution of indoles with tetronic acid and N-acetyltetramic acid mediated by BF3·OEt2 was investigated. This strategy allowed for the preparation of nine indole-substituted furan-2-ones (indolyl-γ-lactones) and 3-pyrrolin-2-ones (indolyl-γ-lactams) and is more straightforward than previously reported synthetic methods. During the course of our investigation, we also discovered a facile synthesis of tetronates and a tetramate via a BF3-mediated addition of alcohols to tetronic acid and N-acetyltetramic acid, respectively.
Selective synthesis of benzyl enol ethers of β-dicarbonyl compounds in basic condition and the application towards synthesis of naphthoquinones
Katakawa, Kazuaki,Yonenaga, Dai,Terada, Tomoyo,Aida, Naoya,Sakamoto, Airi,Hoshino, Keishi,Kumamoto, Takuya
, p. 817 - 825 (2016/11/13)
Selective synthesis of benzyl enol ether of β-tetronic acids and β-dicarbonyl compounds in basic condition was examined. Benzylation of α-methyl-β-tetronic acid with benzyl tosylate in the presence of potassium carbonate gave the corresponding benzyl enol ether exclusively. The reaction of β-tetronic acid and cyclic 1,3-diketones gave the O-benzyl adducts preferentially than the C,O-dibenzylated ones. Diels-Alder reaction of furan derived the benzyl enol ether of α-methyl-β-tetronic acid and benzyne furnished the functionalized napthoquinone derivatives.
Synthesis of vulpinic and pulvinic acids from tetronic acid
Bourdreux, Yann,Bodio, Ewen,Willis, Catherine,Billaud, Célia,Le Gall, Thierry,Mioskowski, Charles
, p. 8930 - 8937 (2008/12/22)
A common precursor, tetronic acid, was used in the synthesis of several vulpinic acids and pulvinic acids, which are pigments found in several lichens and mushrooms. The key features of this method are a two-step alkylidenation of benzyl tetronate and a Suzuki-Miyaura cross-coupling. The synthesis of several natural products, vulpinic acid, pinastric acid, xerocomic acid is described.
Flexible synthesis of vulpinic acids from tetronic acid
Willis, Catherine,Bodio, Ewen,Bourdreux, Yann,Billaud, Célia,Gall, Thierry Le,Mioskowski, Charles
, p. 6421 - 6424 (2008/02/12)
Several vulpinic acids were synthesized in a few steps from a single precursor, the tetronic acid. This commercial compound was converted in a few steps to an iodide. Suzuki-Miyaura cross-couplings involving this common intermediate and various arylboronates allowed to gain access to several vulpinic acids (or methyl pulvinates). Among them, two natural products, vulpinic acid and pinastric acid, were prepared.
Highly efficient 4-O-alkylations of tetronic acids involving oxyphosphonium intermediates
Paintner, Franz F.,Allmendinger, Lars,Bauschke, Gerd
, p. 83 - 86 (2007/10/03)
4-Alkoxy-5H-furan-2-ones were prepared in fair to high yields by regioselective 4-O-alkylation of tetronic acids with stoichiometric amounts of primary and secondary alcohols. This approach involves the intermediacy of (5-oxo-2,5-dihydrofuran-3-yloxy) phosphonium trifluoromethanesulfonates, which were generated in situ on reaction of tetronic acids with triphenylphosphonium anhydride trifluoromethanesulfonate (Hendrickson's reagent).
