50598-33-9Relevant academic research and scientific papers
Synthesis of Cyclic Anhydrides via Ligand-Enabled C–H Carbonylation of Simple Aliphatic Acids
Herron, Alastair N.,Yu, Jin-Quan,Zhuang, Zhe
supporting information, p. 16382 - 16387 (2021/06/23)
The development of C(sp3)–H functionalizations of free carboxylic acids has provided a wide range of versatile C?C and C?Y (Y=heteroatom) bond-forming reactions. Additionally, C–H functionalizations have lent themselves to the one-step preparation of a number of valuable synthetic motifs that are often difficult to prepare through conventional methods. Herein, we report a β- or γ-C(sp3)–H carbonylation of free carboxylic acids using Mo(CO)6 as a convenient solid CO source and enabled by a bidentate ligand, leading to convenient syntheses of cyclic anhydrides. Among these, the succinic anhydride products are versatile stepping stones for the mono-selective introduction of various functional groups at the β position of the parent acids by decarboxylative functionalizations, thus providing a divergent strategy to synthesize a myriad of carboxylic acids inaccessible by previous β-C–H activation reactions. The enantioselective carbonylation of free cyclopropanecarboxylic acids has also been achieved using a chiral bidentate thioether ligand.
Anti-AIDS agents 81. design, synthesis, and structure-activity relationship study of betulinic acid and moronic acid derivatives as potent HIV maturation inhibitors
Qian, Keduo,Kuo, Reen-Yun,Chen, Chin-Ho,Huang, Li,Morris-Natschke, Susan L.,Lee, Kuo-Hsiung
experimental part, p. 3133 - 3141 (2010/09/18)
In our continuing study of triterpene derivatives as potent anti-HIV agents, different C-3 conformationally restricted betulinic acid (BA, 1) derivatives were designed and synthesized in order to explore the conformational space of the C-3 pharmacophore. 3-O-Monomethylsuccinyl-betulinic acid (MSB) analogues were also designed to better understand the contribution of the C-3′ dimethyl group of bevirimat (2), the first-in-class HIV maturation inhibitor, which is currently in phase IIb clinical trials. In addition, another triterpene skeleton, moronic acid (MA, 3), was also employed to study the influence of the backbone and the C-3 modification toward the anti-HIV activity of this compound class. This study enabled us to better understand the structure-activity relationships (SAR) of triterpene-derived anti-HIV agents and led to the design and synthesis of compound 12 (EC50: 0.0006 μM), which displayed slightly better activity than 2 as a HIV-1 maturation inhibitor.
SYNTHESIS OF 4,4- AND 5,5-DISUBSTITUTED 4,5-DIHYDRO-6H-CANTHIN-6-ONES
Hajicek, Josef,Holubek, Jiri,Trojanek, Jan
, p. 2749 - 2762 (2007/10/02)
The paper describes regiospecific synthesis of 4,4- and 5,5-disubstituted 4,5-dihydro-6H-canthin-6-ones III and XVIII, starting from half-esters of 2,3-disubstituted succinic acids, V and XIV.The formation of the anomalous 5,5-disubstituted canthin-4,6-diones XVII is ascribed to oxidation of the intermediate XIX.The 1H NMR spectra of the compounds prepared are discussed.
