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This thesis describes the work performed by the author during PhD studies at FSU. The first two chapters present the summary of the studies done trying to accomplish the first total synthesis of aldingenin B - a natural product first isolated in 2003. While our studies were ongoing, some additional information on the structure of the natural product emerged, therefore our studies and their relationship with the literature available up to 2015 are discussed in detail. Chapters 3 through 6 represent the main topic of the thesis. They focus on the studies directed towards the development of the efficient synthesis of ent-progesterone - a potential drug candidate for the treatment of traumatic brain injury. Chapter 3 introduces the problem and the necessity for such synthesis and reviews the literature relevant to the topic. Chapter 4 presents an improved synthesis of rac-progesterone - an important step in the synthesis of ent-progesterone. Chapter 5 compares the efficiency of the two approaches: an old one and the improved route.