93904-00-8Relevant articles and documents
Preparation of 2,3,3-Triarylacrylic Acid Esters Using Suzuki-Miyaura Coupling Reactions
Cardinal, Sébastien,Voyer, Normand
, p. 1202 - 1216 (2016)
We report here a new strategy to produce 2,3,3-triarylacrylic acid esters, a class of 1,2,2-triarylethene compounds with an α,β-unsaturated ester functionality. Our approach requires the preparation of a gem-dibromoalkene precursor from an α-keto ester, followed by the installation of two aryl groups by Suzuki-Miyaura coupling reactions on the two C-Br bonds. Many 2,3,3-triarylacrylic acid esters with one, two, or three different aryl groups were obtained with complete regio- and stereocontrol in most cases.
Total synthesis of quebecol
Cardinal, Sébastien,Voyer, Normand
supporting information, p. 5178 - 5180 (2013/09/02)
We report here the total synthesis of quebecol, a new polyphenolic compound with potential applications recently isolated from maple syrup and produced during the condensation of the tree acer saccharum's sap. The synthetic approach we developed involves, as key steps, the formation of a dibromoalkene from an α-ketoester precursor followed by a double Suzuki-Miyaura reaction to unite the three aromatic rings of the target compound on a tetrasubstituted olefin precursor. Our methodology is an efficient pathway to the target compound and leads the way for future analogs.
