Furanylidene Systems From A Tosylic Acid-Mediated, Tandem Desilylation-Cyclization Reaction Of Silyl Ethers Of Monoalkynylated Beta-Keto Carbonyls

Single isomers of the furanylidene system 8 were synthesized in four steps. The synthesis begins with the dianion of beta-keto carbonyls and culminates in a mild, tandem desilylation-cyclization reaction using tosylic acid. Compounds synthesized in this study have the potential for further diversification at the alkyne, carbonyl and enol-ether moieties. Hence, the furanylidenes from this study are prospective building blocks for biologically active, furan-containing natural products and their analogs.