Abstract:  

Species of plants within the Salvia genus of the Lamiaceae family are found on nearly every continent and are renowned for their applications in traditional medicine. These plants possess a variety of chemical constituents that can be divided into several groups, the largest of which are the abietane diterpenoids. The first part of the dissertation describes the abietane diterpenoid known as plebeianiol A and details our synthetic endeavor to elucidate the structure of this natural product. 

Over the last twenty years, hydrofunctionalization of alkenes by metal-hydride hydrogen atom transfer (MHAT) has emerged as an exceptionally useful tool in synthetic organic chemistry. The second part of the dissertation describes the development of a novel MHAT-initiated annulation cascade between allylarenes and electron deficient alkenes. The reaction is thought to proceed via radical/polar crossover and enables access to functionalized tetralins that are the formal products of the largely infeasible Diels–Alder cycloadditions of styrenes.

Owing to their striking molecular architectures and broad biological activities, sesterterpenoid natural products have long attracted the interests of organic chemists. The third part of the dissertation will describe our investigative studies towards the sesterterpenoid natural product known as asperterpenoid A. Isolated in small quantities from a mangrove fungus in 2013, asperterpenoid A displays useful inhibitory activity against Mycobacterium tuberculosis. A synthesis of this poorly abundant natural product could inform the rational development of novel therapeutics targeting the ancient disease, tuberculosis.