Terpenoids represent by far the most structurally and functionally diverse category of specialized metabolites found in Nature. In spite of their complexity, terpenes all share a very similar biosynthesis, which involves a cascade reaction of a simple linear polyolefin precursor undergoing multiple carbon-carbon bond-forming additions of carbocations to neighbouring alkene functions. This cascade results in the production of a rigid, structurally well-defined three-dimensional scaffold. These scaffolds then serve as versatile molecular recognitions platforms which can be fine-tuned - over millions of years of evolution - through a wide range of iterations, exploring different oxygenation and derivatisation patterns. In directed chemical synthesis, as in medicinal chemistry or natural product synthesis, a similar synthesis strategy would be highly effective but is challenging to achieve. Biomimetic approaches are highly limited because cascade cyclisations not occurring within the hydrophobic binding site of an enzyme have a much higher propensity to undergo side reactions. This is why terpene scaffolds are usually built via a long sequence of fragment-coupling reactions, gradually building molecular complexity via discrete well-controlled bond formation steps. In this project, a hybrid approach towards terpene synthesis will be explored wherein carbocyclic scaffolds can be assembled by designing intermolecular cascade reactions between simple linear or monocyclic fragments.