Part 1: Synthesis of Psico-nucleoside Analogs of Oxetanocin A. Part 2: Synthesis of Alpha-glycosphingolipids for in Vivo Studies and Purity Determination

Date of Award


Document Type


Degree Name

Doctor of Philosophy (Ph.D.)

Institution Granting Degree

University of Connecticut

Cedarville University School or Department

Science and Mathematics

First Advisor

Amy R. Howell


Pure sciences, Oxetanocin, Glycosphingolipids, psico-nucleosides, Methyleneoxetane


Oxetanocin A, isolated in 1986 from the fermentation broth of Baccilus megaterium , was the first reported, naturally occurring nucleoside that contained an oxetane as the sugar moiety. This novel nucleoside also demonstrated potent anti-viral activity against HSV-1, HSV-2, HCMV and HIV-1. Herein, we report the first synthesis of a psico -nucleoside analog of oxetanocin A by utilizing the reactivity of Selectfluor® , an electrophilic fluorine source, with an α-methylene-oxetane.

α-Glycosphingolipids (GSLs) have found much attention for their ability to modulate immune responses. The interest in this field continues to grow. Pharmalogically active GSLs and labeled GSLs are essential for studying their role immune responses and can lead to the development of new approaches to treating cancer and other autoimmune diseases. This thesis describes the synthesis of GSLs designed to aid in the investigation of NKT cell stimulation.