293743-95-0Relevant academic research and scientific papers
Synthesis and 19F NMR parameters of a perfluoro-tert-butoxy tagged L-DOPA analogue
Capuani, Silvia,Cavazzini, Marco,Ciardello, Andrea,Orlandi, Simonetta,Pozzi, Gianluca
, (2020)
The robust multistep synthesis of a perfluoro-tert-butoxy (PFTB) tagged analogue of the non-proteinogenic amino acid 3,4-dihydroxy-L-phenylalanine (L-DOPA) via diastereoselective benzylation of Oppolzer's sultam glycinate was developed. The new compound is characterized by a flexible alkoxy linker connecting PFTB to the biochemically and pharmacologically relevant L-DOPA scaffold, which facilitates the free motion of the fluorinated moiety. Therefore, the nine chemically equivalent fluorine atoms give rise to an intense and sharp 19F NMR singlet signal that is easily detected in an aqueous environment. In addition, the kinetics of 19F NMR relaxation processes in blood solution fit the requirements for the potential use of the new compound as a probe in 19F magnetic resonance imaging applications in translational clinical field.
Toward a total synthesis of stigmatellin; Obtention of an advanced fragment from gallic acid
Domon,Uguen
, p. 5501 - 5505 (2007/10/03)
Treatment by a base, then an acid, of the ester 3, which was prepared by starting from gallic acid 7a, afforded the chromone 6c, whose Swern oxidation, followed by condensation of the resulting aldehyde 6a with the trienyl lithium derivative 13b and methyl iodide, furnished products isomeric with, but not strictly identical to, an authentic sample of O-benzyl stigmatellin 1c. (C) 2000 Elsevier Science Ltd.
