Two major motivations can be attributed to natural product total synthesis: a search for function, and the development of strategies for complex molecule synthesis. The work described in this dissertation covers both topics with critical analysis of methodologies and synthesis practices. Chapter 1 provides a statement on the current field of total synthesis highlighting enduring contributions, motivations, and future directions. Chapters 2 and 3 focus on two total synthesis projects that arose as part of a collaboration in the Sarpong group with scientists at Corteva Argriscience for the identification and development of natural products as antifeedant molecules—a search for function. Chapter 2 describes the total synthesis and biological evaluation of xiamycin-type indolosesquiterpenoids utilizing a ‘benzannulation of carvone strategy’. Chapter 3 discusses progress toward broadening this synthesis strategy to paspaline-type indole diterpenoids. Chapters 4 and 5 initiate a discussion on strategy and tactics in synthesis. Chapter 4 focuses on symmetry inspired strategies and symmetry tactics, the distinction between the two, and how they can each be greatly simplifying in synthesis. Chapter 5 expands on classifications of C–H oxidation reactions, examines their use in natural product synthesis, and gives insights into their strategic application through case study analysis. Chapter 6 details progress toward the synthesis of the polyprenylated acylphloroglucinol natural products melicolones A & B utilizing a hidden symmetry strategy. Chapter 7 discusses a broad approach toward several bicyclic natural product cores through the divergent C–C cleavage of a common intermediate—the development of strategies for complex molecule synthesis. Overall, this work explores studies in indoloterpene function as well as symmetry and C–C cleavage strategies for complex molecule synthesis.