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.
Vetica, F., De Figueiredo, R.M., Cupioli, E., Gambacorta, A., Loreto, M.A., Miceli, M., et al. (2016). First asymmetric organocatalyzed domino Friedel-Crafts/lactonization reaction in the enantioselective synthesis of the GABAB receptor modulator (S)-BHFF. TETRAHEDRON LETTERS, 57(7), 750-753 [10.1016/j.tetlet.2016.01.015].
First asymmetric organocatalyzed domino Friedel-Crafts/lactonization reaction in the enantioselective synthesis of the GABAB receptor modulator (S)-BHFF
VETICA, FABRIZIO;GAMBACORTA, Augusto;MICELI, MARTINA;GASPERI, TECLA
2016-01-01
Abstract
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
