Browsing by Subject "Lactonization"

Now showing 1 - 2 of 2
  • Thumbnail Image
    Item
    Model studies, methodologies, and progress toward a synthesis of Lyngbyaloside B.
    (2010-07) May, Aaron Elijah
    The bulk of the work done in this thesis falls into the categories of studying acylketene intermediates and developing strategies toward the synthesis of lyngbyaloside B. In the first chapter, a model system of lyngbyaloside B and lyngbouilloside was created to study the dual macrolactonization/pyran-hemiketal formation reaction. In the second chapter, methods for the efficient creation of acylketene intermediates at room temperature were advanced. In the third chapter, the selectivity of additions to acylketene was explored. In the fourth chapter, an aldol method useful to the synthesis of lyngbyaloside B was explored, leading to the discovery of a novel decarboxylative isomerization, which was also explored. In the fifth chapter, progress toward the total synthesis of lyngbyaloside B is presented. Lastly, the sixth chapter involves studies that do not cleanly fit into the previous 5 chapters.
  • Thumbnail Image
    Item
    Synthetic efforts toward a total synthesis of (+)-Pelorusdie A.
    (2009-06) Kopel, Lucas C.
    This thesis has been divided into six chapters that describe synthetic efforts toward the cytotoxic marine macrolide (+)-peloruside A, isolated by Northcote and coworkers from the New Zealand marine sponge Mycale hentscheli. Chapter 1 discusses the background of peloruside A and published literature studies relating to its biological activity. Chapter 2 conveys a detailed report of the synthetic efforts by others that have resulted in three total syntheses and multiple efforts toward the total synthesis of peloruside A. Chapter 3 describes the previous synthetic efforts by Hoye group members toward peloruside A. Two different strategies for synthesizing the C13-C20 fragment of (+)-peloruside A have been established using ring-closing metathesis. Synthesis of the C1-C9 fragment of (+)-peloruside A was accomplished using a kinetic lactonization strategy. Chapter 4 reports on my efforts at scaling-up and optimizing the synthesis of the C1-C9 fragment of (+)-peloruside A and modifications to the previous route. Chapter 5 describes the new progress toward synthesizing (+)-peloruside A that was achieved. These efforts culminated in the synthesis of a C1-C11 fragment of (+)-peloruside A along with studies investigating the coupling of late stage segments via a 1,5-anti boron-mediated aldol. Chapter 6 highlights the key features of my synthetic efforts toward (+)-peloruside A.