Stereoselective synthesis of E-3-(arylmethylidene)-5-(alkyl/aryl)-2(3H)-furanones by sequential hydroacyloxylation-Mizoroki–Heck reactions of iodoalkynes†,10.1039/C8OB02063A

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Stereoselective synthesis of E-3-(arylmethylidene)-5-(alkyl/aryl)-2(3H)-furanones by sequential hydroacyloxylation-Mizoroki–Heck reactions of iodoalkynes†

Gopinathan Muthusamy,Sunil V. Pansare

Organic & Biomolecular Chemistry Pub Date : 10/10/2018 00:00:00 , DOI:10.1039/C8OB02063A

Abstract

A modular, stereoselective synthesis of E-3-(arylidene)-5-(alkyl/aryl)-2(3H)-furanones was developed. The methodology features regioselective addition of β-aryl acrylic acids to iodoacetylenes to furnish the Z-acyloxy iodoalkenes. A stereoselective 5-exo-trig Mizoroki–Heck reaction of the acyloxy iodoalkenes generates the target E-2(3H)-furanones. The approach was applied in a formal synthesis of the naturally occurring kinase inhibitor BE-23372M.