Guaiane natural products are complex architectures that contain multiple stereogenic centers, ring junctures, and functionalities that render their synthesis difficult without an efficient and effective methodology. Herein, a new method for generating these natural products will be discussed. In particular, highly strained intermediates, generated through an intramolecular cyclobutadiene cycloaddition, will be studied and utilized. The following are a summary of the chapters: Chapter 1: Tricyclo[3.2.0.02,4]heptanes are unique scaffolds that possess many interesting chemistries. A review of both their synthesis and chemistry is covered. Chapter 2: Syn-tethered tetracyclo[5.3.0.01,5.02,4]decanes are strained systems obtained through a cyclobutadiene cycloaddition-intramolecular cyclopropanation sequence. Studies related to these systems will be covered. Chapters 3

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