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

Autor: Muthusamy G; Department of Chemistry, Memorial University, St. John's, Newfoundland, Canada A1B 3X7. spansare@mun.ca., Pansare SV
Jazyk: angličtina
Zdroj: Organic & biomolecular chemistry [Org Biomol Chem] 2018 Oct 31; Vol. 16 (42), pp. 7971-7983.
DOI: 10.1039/c8ob02063a
Abstrakt: 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.
Databáze: MEDLINE