| The term "meroterpenoids" refers to natural products that contain both terpenoid and non-terpenoid components. This term encompasses a massive body of naturally occurring organic molecules, diverse in molecular constitution and biological activity. As methods for isolation and structure elucidation have grown in sophistication, so too have methods for the laboratory synthesis of many meroterpenoid targets.;This thesis work was carried out with the ultimate goal of devising a means for efficient synthetic access to this class of meroterpenoids. Along the way, a number of pitfalls were encountered, but valuable insight was gained which should enable further pursuit of this elusive natural product family.;Described herein are various strategies and tactics examined for the pursuit of meroterpenoid (polyketide-terpenoid) natural products. Chapter 1 provides a literature review of the relevant meroterpenoid natural products that were the subject of study for this thesis research. With simplicissin as its focal point, Chapter 2 provides a review of various approaches that were examined in an aim to gain a foothold into this as-yet unassailable fungal meroterpenoid metabolite family. Chapter 3 describes the application of Minisci-type reactivity of boronic acids to practical radical cyclizations, and the successful implementation of this method for the preparation of ent-chromazonarol (and analogs thereof). This convergent approach to meroterpenoid synthesis has the potential to be applied to other classes beyond the quinone-sesquiterpenoids, including the tetraketide-sesquiterpenoids described in Chapters 1 and 2. |
