Bengazole A is a highly potent antifungal agent from a marine sponge of the genus Jaspis sp. The structure of bengazole A contains a bis-(oxazolyl)methanol moiety which is an unprecedented motif among natural products. In addition, bengazole A is the only known marine natural product that contains a C5 monosubstituted oxazole. This dissertation research describes work towards the total synthesis of bengazole A and the development of new synthetic methodology.Chapter 2 details the initial work on the synthesis of bengazole A including the attempted synthesis of the undescribed 2-formyloxazoline. While efforts to prepare a 2- formyloxazoline were unsuccessful, a novel oxidative rearrangement of 2-methyloxazoline to a dihydrooxazinone was discovered.Chapter 3 develops the methodology of the oxazoline-dihydrooxazinone oxidative rearrangement, describes the chemistry of 3-unsubstituted dihydrooxazinones, and utilizes the oxidative rearrangement for the synthesis of optically pure (S)-tert-leucine. The mechanism of the oxidative rearrangement was investigated by kinetic studies, isolation of an intermediate, and 13C labeling studies. These studies led to refinement of the proposed mechanism of reaction.Chapter 4 describes the preparation of an advanced intermediate incorporating C1-C9 of bengazole A by taking advantage of the ambident nucleophilicity of 2-lithiooxazole with preferential C4 addition to aldehydes. The aldehyde used in the synthesis, a precursor to the bengazole side chain, C1-C6, was prepared from the inexpensive sugar D-galactose.Chapter 5 outlines a synthetically useful preparation of C5 monosubstituted oxazoles for incorporation in the last stage of bengazole A synthesis. The methodology allows selective deprotonation-electrophilic addition at C5 of 2-methylthiooxazole for the construction of 5-substituted oxazoles. The methylthio group is then conveniently removed by reductive desulfurization with Raney nickel
