Evaluation of ‘east-to-west’ ether-forming strategies for the total synthesis of maoecrystal V

Model systems that evaluated different approaches to construct the central ether ring of maoecrystal V are described. Our first model systems attempted the ether formation using C–H functionalization reactions, which led to interesting rearrangements but none of the desired ether product. An intramolecular conjugate addition strategy was then explored that successfully formed the targeted C–O bond but resulted in the undesired stereochemistry.