5446-02-6Relevant articles and documents
Total Synthesis of (+/-)-Ovalicin
Corey, E. J.,Dittami, James P.
, p. 256 - 257 (1985)
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Catalytic Carbochlorocarbonylation of Unsaturated Hydrocarbons via C?COCl Bond Cleavage**
Boehm, Philip,Denton, Elliott H.,Fellert, Maximilian,Lee, Yong Ho,Morandi, Bill,Roediger, Sven
supporting information, p. 23435 - 23443 (2021/09/20)
Here we report a palladium-catalysed difunctionalisation of unsaturated C?C bonds with acid chlorides. Formally, the C?COCl bond of an acid chloride is cleaved and added, with complete atom economy, across either strained alkenes or a tethered alkyne to generate new acid chlorides. The transformation does not require exogenous carbon monoxide, operates under mild conditions, shows a good functional group tolerance, and gives the isolated products with excellent stereoselectivity. The intermolecular reaction tolerates both aryl- and alkenyl-substituted acid chlorides and is successful when carboxylic acids are transformed to the acid chloride in situ. The reaction also shows an example of temperature-dependent stereodivergence which, together with plausible mechanistic pathways, is investigated by DFT calculations. Moreover, we show that benzofurans can be formed in an intramolecular variant of the reaction. Finally, derivatisation of the products from the intermolecular reaction provides a highly stereoselective approach for the synthesis of tetrasubstituted cyclopentanes.
Synthesis, structure, and anion binding of functional oxacalix[4]arenes
Ma, Jiao-Xia,Fang, Xu,Xue, Min,Yang, Yong
, p. 5075 - 5085 (2019/06/03)
Oxacalix[4]arenes obtained from the highly efficient, one-pot SNAr reaction were post-macrocyclization functionalized through the reduction of nitro groups and hydrolysis of the ester groups to obtain several derivatives of desired solubility. The difficulties in basic hydrolysis of ester groups were overcome via developing an acid hydrolysis method for tert-butyl ester derivatives of this class. The synthesis of symmetrical oxacalix[4]arenes from an unsymmetrically substituted precursor was also explored via a multiple step fragment coupling approach. Compounds 17 & 18 adopted 1,3-alternate conformations in the solid state as most oxacalix[4]arenes did, and a chair (zigzag) conformation was revealed for tetraamido oxacalix[4]arene (6a) by X-ray single crystal analysis. The tetraureido oxacalixarene (7) showed strong association towards various anions such as F-, Cl-, Br-, I-, Ac-, and HSO4- with a 1:1 stoichiometry as revealed by 1H NMR analysis and UV-vis measurements.
Bavachinin analogues as agonists of pan-peroxisome proliferator-activated receptors
Yi, Jingyu,Du, Guoxin,Zhao, Yuanyuan,Zhang, Liuqiang,Li, Bo,Zhu, Weiliang,Huang, Cheng,Li, Yiming,Guo, Fujiang
, p. 1851 - 1862 (2018/06/18)
Peroxisome proliferator-activated receptors (PPARs) agonists contribute to the regulation of glucose, lipid, and cholesterol metabolism and have emerged as key targets to treat metabolic syndrome. In our previous study, the natural compound bavachinin was found to have pan-PPAR agonist activity. In this study, five isoflavones, three isoflavanones, and five scaffold-hopping analogues of bavachinin were designed, synthesised, and evaluated through reporter gene assays for pan-PPAR agonist activity. The analogue 2-(4-hydroxyphenyl)-6-isopentenyl-7-methoxy-2,3-dihydroquinolin-4(1H)-one (21) was identified as a pan-PPAR agonist, exhibiting substantially higher PPAR α/β agonist activity and equal PPAR-γ agonist activity than does bavachinin.