We have recently described synthetic routes to the azaspirocyclic ring systems found in marine tricyclic alkaloids such as Cylindricine A utilising a Ru-alkylidene cross-metathesis reaction and acid-catalysed cyclisation. Construction of the third ring, however, requires cross coupling of a highly hindered, α-substituted methylenecycloalkane. CM of such olefins is highly challenging. This paper describes a generic steric-reversal strategy that can be used to react previously unreactive, sterically demanding alkenes using commercially available catalyst.