New perspectives for Lewis acid-catalyzed [2+2] cycloadditions of allenoates

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The objective of this proposal is the synthesis of hebelophyllene E, a naturally occurring sesquiterpene, which was isolated from the ectomycorrhizal fungus Hebeloma longicaudum in the late 1990s. In the context of this project, we have developed an enantioselective Lewis-acid catalyzed [2+2] cycloaddition followed by a ligand controlled copper hydride reduction to access the cis-fused cyclobutane motif. Thus, the goal is to apply these findings in the synthesis of hebelophyllene E and demonstrate that our methodology can be used early in a synthetic sequence as well as late stage using highly functionalized alkenes.