Abstract
Isolated from the Aspergillus species TJ17 of fungi, spiroaspertrione A features a novel spiro[bicyclo[3.2.2]nonane-2,1′-cyclohexane] carbocyclic core and was shown to possess fascinating antibacterial activity, including the potentiation of oxacillin against methicillin-resistant Staphylococcus aureus. This thesis describes several strategies aimed towards the first total synthesis of the meroterpenoid.