A stereoselective and atom-efficient approach to multifunctionalized five- and six-membered rings via a novel Michael-initiated intramolecular Diels-Alder furan reaction

A variety of key precursors to the intramolecular Diels-Alder reaction of furan diene (IMDAF) are prepared via a very facile 1,4-addition of O-, S-, N-, and C-entered nucleophiles possessing unsaturated tether to beta-furyl nitroethylene. Subsequent IMDAF reaction of the 1,4-adducts, carried out under thermal conditions, provided five- and six-membered carbocycles and heterocycles fused to an easily cleavable oxabicycloheptane moiety.