The total synthesis of (–)-herbaric acid has been achieved through the stereoselective synthesis of 3-substituted isobenzofuranones with a new organocatalytic route. When combined with a catalytic amount of benzoic acid, quinidine thiocarbamate bifunctional catalysts have demonstrated their efficiency for the diastereoselective halolactonization reaction of acrylate-type benzoic acids bearing a chiral alkoxycarbonyl group on the carbon-carbon double bond. High diastereomeric excesses were obtained thanks to a positive match effect between the (+)-menthyl ester group and the chiral organocatalyst.
Previous Article in event
Synthesis and Characterization of a Melamine-modified Hydrogel: The Study of Doxorubicin Slow ReleasePrevious Article in session
Next Article in event
Total synthesis of (–)-herbaric acid through organocatalyzed asymmetric halolactonization of acrylate-type benzoic acids.
Published: 03 November 2017 by MDPI in The 21st International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis
Keywords: Asymmetric organocatalysis, Cinchona alkaloids, halolactonization reaction, 3-substituted isobenzofuranones