1. Sulfone-based Methodology for the Construction of Biologically Relevant Furans
S. Shaun Murphree, Department of Chemistry, Allegheny College, Meadville, PA
2,3-Dibromo-1-phenylsulfonyl-1-propene (DBP) is a multifunctional shelf-stable sulfone reagent which reacts with a variety of nucleophiles.
DBP reacts with unsymmetrical methyl 1,3-diketones in the presence of methanolic sodium hydroxide to give an adduct which suffers selective deacylation and subsequent cyclization to form 2-alkyl-4-phenyl-sulfonylmethyl furans. These products can be further elaborated by alkylation and reductive desulfonylation to give 2,4-dialkylfurans. On the other hand, an aerobic oxidative desulfonylation leads to 5-alkyl-3-furoic acids.