Short electrochemical asymmetric synthesis of (+)- N -acetylcolchinol Yi Du, Adelaide Lunga and Andrei V. Malkov Loughborough University, UK
A short synthesis of N -acetylcolchinol using a greener and step-economical pathway is reported where all the redox reactions, except for the asymmetric reduction, were carried out electrochemically, replacing protocols that employ transition metals or stoichiometric hazardous reagents. In a 4-step racemic sequence, chemoselective reduction of chalcone and intramolecular oxidative arene–arene coupling were performed in an electrochemical cell giving the target N -acetylcolchinol with an overall 41% yield. In a 7-step asymmetric variant, electrochemistry was also employed for the deprotection of p -methoxyphenyl amine. The target compound was obtained with a 33% overall yield and 99.5 : 0.5 er.
References 1. Y. DU, A. Lunga, A.E. Rubtsova and A.V. Malkov, Green Chemistry , 2022 , DOI: 10.1039/D2GC02321K.
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© The Author(s), 2022
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