Applications of a hydroxy-directed Diels-Alder reaction and further investigation of the tandem oxy-CopeEne, and oxy-CopeEneClaisen reactions

Abstract

The recent development of a hydroxy-directed Diels-Alder reaction, which enables control of both regio- and diastereoselectivity, has prompted an investigation of potential applications. Extending the methodology to more complicated dienes, such as those created via the tandem oxy-Cope/Ene reaction, offers the potential for rapid construction of polycyclic molecules with significant stereochemical complexity.* The simplicity and efficiency of this technique has also inspired its employment as the primary disconnection in the production of a library of analogues of the unsaturated dialdehyde Isovelleral.* Also examined herein is the recently discovered tandem oxy-Cope/Ene/Claisen reaction; a highly diastereoselective method for generating trans -decalin systems containing quaternary carbon centers. Showing potential as a tool in diterpene synthesis, the scope and limitations of this reaction were further investigated by attempting the synthesis of a rosane derivative 97, recently isolated from the liverwort Gackstroemia decipiens .* *Please refer to dissertation for diagrams.