1451148-39-2

Upstream product

• 52058-11-4 ethyl 4-hydroxy-3-methoxymandelate 
• 93904-00-8 ethyl 4-(benzyloxy)-3-methoxymandelate 
• 7368-78-7 4-bromoguaiacol 
• 90-05-1 2-methoxy-phenol 
• 63057-72-7 2-benzyloxy-5-bromoanisole 
• 95-92-1 oxalic acid diethyl ester 

Downstream Products

• 1415803-96-1 ethyl 2,3,3-tri-(4-hydroxy-3-methoxyphenyl)propanoate 
• 1360605-46-4 4,4',4''-(3-hydroxypropane-1,1,2-triyl)tris(2-methoxyphenol) 
• 1451148-37-0 ethyl 2,3,3-tri(4-benzyloxy-3-methoxyphenyl)prop-2-enoate 
• 1451148-38-1 ethyl 3,3-dibromo-2-(4-benzyloxy-3-methoxyphenyl)prop-2-enoate 

Relevant academic research and scientific papers

Total synthesis of quebecol

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.

Rapid Bis-Coupling Reactivity with Triarylbismuth Reagents: Synthesis of Structurally Diverse Scaffolds and Step-economic Convergent Synthesis of Quebecol

The cross-coupling study of gem-dibromoesters with triarylbismuths as threefold arylating reagents was investigated under palladium-catalyzed conditions. This study using triarylbismuth reagents explored the cross-coupling reactivity with various functionalized gem-dibromoesters. It furnished a variety of multi-functional trisubstituted acrylates embedded with aryl, alkene and alkyne scaffolds in high yields. The present study in turn, provided easy access to various triarylated acrylates and functionalized 1,3-dienyl and 1,3-enyne esters. Further, the established method applied in the step-economic and convergent synthesis of quebecol natural product in good yield.

Preparation of 2,3,3-Triarylacrylic Acid Esters Using Suzuki-Miyaura Coupling Reactions

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.