123557-91-5Relevant articles and documents
First asymmetric organocatalyzed domino Friedel-Crafts/lactonization reaction in the enantioselective synthesis of the GABAB receptor modulator (S)-BHFF
Vetica, Fabrizio,De Figueiredo, Renata Marcia,Cupioli, Emilia,Gambacorta, Augusto,Loreto, M. Antonietta,Miceli, Martina,Gasperi, Tecla
, p. 750 - 753 (2016)
An asymmetric domino Friedel-Crafts/lactonization sequence between phenols and trifluoropyruvate has been accomplished for the first enantioselective synthesis of (S)-BHFF, a positive allosteric modulator (PAM) of GABAB receptor. The developed protocol leads to 3-OH-benzofuranone derivatives bearing a quaternary stereogenic center, and gives a valuable access to bioactive compounds with promising pharmaceutical applications.
Catalytic Friedel-Crafts/lactonization domino reaction: Facile access to 3-Hydroxybenzofuran-2-one scaffold
Vetica, Fabrizio,Pelosi, Alessandra,Gambacorta, Augusto,Loreto, M. Antonietta,Miceli, Martina,Gasperi, Tecla
, p. 1899 - 1906 (2014/04/03)
A valuable Lewis-acid-catalysed domino reaction involving a Friedel-Crafts alkylation of variously substituted phenols followed by a direct lactonization has been successfully developed (22 examples, yields up to 98 %). This protocol tolerates not only op
Efficient one-pot synthesis of the GABAB positive allosteric modulator (R,S)-5,7-Di-tert-butyl-3-hydroxy-3-trifluoromethyl-3H-benzofuran-2- one
Alker, Andre M.,Grillet, Francois,Malherbe, Pari,Norcross, Roger D.,Thomas, Andrew W.,Masciadri, Raffaello
, p. 3398 - 3405 (2008/12/23)
The GABAB positive allosteric modulator (R,S)-5,7-di-tert-butyl- 3-hydroxy-3-trifluoromethyl-3H-benzofuran-2-one (1) was synthesized in one pot from the anhydrous lithium salt of 2,4-di-tert-butylphenol and methyl trifluoropyruvate mediated by a stoichiometric amount of anhydrous gallium(III) chloride in 64% overall yield. The enantiomers of 1 were separated by chiral-phase HPLC (Chiralpak AD), and the absolute configuration was determined by X-ray crystallography. Copyright Taylor & Francis Group, LLC.