This study focusses on the [2+2]-photocycloaddition of symmetric polyenic system tethered by an aryl bis-sulfide or sulfone platform. Using direct irradiation or photosensibilization, no expected ladderane product was isolated. In most cases, only tricyclic products including a single cyclobutane moeity were formed. Irradiation of bis-acrylic precursors in water with encapsulation by a host (cyclodextrin or cucurbituril) provided a stereoselective access to valuable cyclobutyl adducts.
The post-functionalization of ketone products originating from the PtCl2-catalyzed cycloisomerization of enynyl esters is described. Post-functionalization is accomplished via diastereoselective alkylation, regioselective cyclopropane opening and regioselective Baeyer–Villiger and Beckmann rearrangements to provide functionalized polycycles.
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