Limno-CP: A Natural Product-inspired 5-Aryl-3(2H)-furanone as Scaffold for a Library of alpha-Modified Enones

Abstract

A library of 5-aryl-3(2H)-furanones that are modified in the α-position of the α,β-unsaturated carbonyl system was prepared via simple one- to three-step transformations from one common scaffold. The ¹³C NMR characterization of the enone system showed a strong influence of the α-substituents, especially on the shifts of the α- and β-carbon atoms. Probing the addition chemistry of nucleophiles versus our α-modified enones, a 1,2-addition-elimination­ was found, but no 1,4-addition.