and Annulation Reactions of α-(Phenylthio) Dicarbonyl Electrophiles with Bis(trimethylsilyl) Enol Ethers: Synthesis of Highly Functionalized Medium Ring Cycles

Article abstract of DOI:10.1021/jo00131a013

The <3+4> and <3+5> annulations of bis(trimethylsilyl) enol ethers with 1,4- and 1,5-dicarbonyl electrophiles bearing α-phenylthio substituents leads to the formation of bicyclic <3.2.1> and <3.3.1> ethers with good regiochemical and stereochemical control.Subsequent oxidation of the phenylthio moiety followed by reduction with SmI2 constitutes a high-yielding and regioselective process for cleavage of the bridging ether linkage.The overal strategy provides a synthetic pathway for the synthesis of highly functionalized medium ring carbocycles.