| Novel synthetic strategies and results to the unique terpene maoecrystal V are discussed.;The first strategy utilizes the reactivity of the carbonyl group in a cascade of three carbonyl dependent reaction. This oxy-Michael/aldol/oxy-Michael approach resulted in an unexpected di-cyclization event resulting in a complex spiro-acetal structure that led to a modification of this approach. The adapted route to maoecrystal V enabled synthesis of a complex intermediate that defied attempts to progress it further towards maoecrystal V.;The second strategy investigated included a 1,5-hydride shift to form the A-ring of maoecrystal V. When this 1,5-hydride shift was shown to be ineffective various modifications, including C-H activation and desymmetrization, were investigated.;This work provides the first synthesis to the desired connectivity of the tetrahydrofuran/delta-lactone/bicycle-[2.2.2]-octane fragment of maoecrystal V. |
