2,4-Cyclohexadien-1-ones in Organic Synthesis. Intramolecular Diels-Alder Reactivity and the Oxa-di-?-methane Photorearrangement of Diels-Alder Adducts

Article abstract of DOI:10.1021/jo00217a015

The preparation and intramolecular Diels-Alder reactions of a series of 6-alkenyl-6-(methoxycarbonyl)2,4-cyclohexadien-1-ones are described.The resulting tricyclic β,γ-enones undergo the oxa-di-?-methane rearrangement to give substrates of potential use in the construction of polyquinane natural products.This methodology provides a means for construction of tetracyclic rings of type A by C-alkylation of the synthetic equivalence of enolate B.