Natural products, optimized through the ages by a vast array of biological organisms, serve an impressive array of functions including means of communication, defense, and attack for their parent organisms. The complex architectures and intricately arrayed functionalities of these molecules, which ultimately impart their biological activity, have for decades served as inspiration to synthetic organic chemists. Today, natural product total synthesis remains an important source of synthetic method and strategy development, expanding the scientific community’s ability to access complex molecules in general. In turn, this bolsters the community’s molecular toolkit enabling an ever-expanding range of applications. Within this context, terpene natural products have been an especially fruitful area of research. In this dissertation, developments towards the syntheses of varied and complex terpenoid natural products will be discussed. In chapter 1, a number of interesting examples of total syntheses of terpenoid natural products are summarized, setting the stage for subsequent discussion of our own contributions to this area. In particular, completed syntheses of ophiobolin and the ophiobolin-derived bipolarolide families of natural products are emphasized. In chapter 2, efforts toward the total synthesis of bipolarolides A and B are described. These include improvements to the racemic synthesis of the B,C,D-tricyclic core of the natural products, development of an intramolecular nitrone [3+2] cycloaddition, development of an asymmetric synthesis of the core, and a multi-decagram scale asymmetric synthesis of the sidechain precursor. In chapter 3, efforts toward the total synthesis of illihenlactoneosides B and C are detailed. An ambitious cyanation / cyclization strategy was developed which gives access to an intermediate with 3 rings and 5 stereocenters as a single enantiomer in just six steps longest linear sequence. This intermediate was then elaborated to a linear triquinane structure which contains functionality to address each of the remaining challenges in the synthesis.