Meroterpenoids are a class of natural products derived from a mixed biosynthetic origin, with an arene entity originating from the polyketide pathway and the polyene unit originating from the terpene pathway. These natural
products display a multitude of biological activities. The Barrett group has reported successful syntheses of meroterpenoid natural products, including those derived from polyene cyclizations. The first part of this thesis studied the chemical space around non-natural acetylenic polyene resorcylates for their reactivity in biomimetic polyene cyclizations, which were synthesized
by means of remote terpene functionalization, acetylene installation with in situ deprotection and established biomimetic polyketide aromatization procedures developed within the Barrett group. The results should be of interest for structure-activity-relationship (SAR) studies and enable future derivatization studies. The second part of this thesis concerns the synthesis of amorfrutin natural products, which was done in collaboration with a final year undergraduate student. Natural products isolated from Amorpha fruticosa display a range of bioactivities with unusual specificity. For SAR purposes, a unified approach was designed to synthesize these natural products. The syntheses followed a biosynthetic proposal of interconversion between the amorfrutins. Thus, the biomimetic strategy of polyketide aromatization enabled the synthesis of amorfrutin B, which in turn displays the core structure of (S)- and (R)-amorfrutin D. Amorfrutin A to amorfrutin C conversion and the synthesis of C5 analogs are described.