UC Irvine

Part I of this dissertation presents the efforts directed towards the total synthesis of batrachotoxin. The general approach focuses on the construction of the C ring of the steroid backbone through two carbon-carbon bond forming reactions. This approach breaks the complex natural product into two more approachable pieces. The AB ring system was accessed from the Hajos-Parish ketone and was coupled to the elaborated D ring by a conjugate addition/Claisen rearrangement sequence to form one of the desired carbon-carbon bonds. Extensive effort has been made in an attempt to cyclize the C ring.

Part II describes the development of a new approach to the synthesis of substituted pyridines. The method aims to provide a reliable synthesis of a diverse scope of substituted pyridines through a concise three step procedure. Readily available enones are first converted into 1,5-dicarbonyls through a two-step Sakurai allylation/oxidative cleavage sequence, which is followed by subsequent cyclization to the corresponding pyridine using hydroxylamine hydrochloride. A variety of substituted pyridines have been synthesized using this method.