Synthesis of epi-oxetin via a 2-methyleneoxetane and progress towards the synthesis of a sulfur analog of KRN7000

Date of Completion

January 2007


Chemistry, Organic




The natural world has supplied mankind with a plethora of biologically interesting compounds, many of which have important roles in everyday life. A vast range of sources are responsible for such substances, and they are found in different environments around the globe. Many natural products are produced in very scarce quantities in nature; therefore, producing them synthetically on a larger scale can be crucial to the determination of their usefulness.^ 2-Methyleneoxetanes are useful intermediates in the synthesis of oxetane-containing systems. Herein, the synthesis of the natural product oxetin via a serine-derived methyleneoxetane, will be described. Oxetin has shown interesting antibacterial and pesticidal activity through the inhibition of glutamine synthetase.^ Natural glycosphingolipids are membrane constituents found most often in the external surface of the plasma membrane in eukaryotic cells. They have been shown to elict potent immune responses via presentation by CD1 proteins, implicating them as possible therapeutic agents for a variety of diseases. Analogs of natural glycosphingolipids are of biological interest, due to the possibility of enhanced activity over their naturally occurring counterparts. In this thesis, the synthesis of a sulfur analog of KRN7000, a potent glycosphingolipid, will be described.^