Synthesis and Characterization of Inosamines

Author

Sing Raj Gurung

Date of Award

12-2006

Degree Name

Master of Science

Department

Chemistry

First Advisor

Dr. Elke Schoffers

Second Advisor

Dr. James Kiddle

Third Advisor

Dr. Sherine Obare

Access Setting

Masters Thesis-Open Access

Abstract

This project is concerned with the preparation of scyllo-inosarnine hydrochloride 6, a biologically active compound, which bears six successive stereogenic centers. The synthesis of this compound would help elucidate the involvement of inosamines in biological nitrogen fixation. myo-Inositol served as the starting material to synthesize target compound 6. Regioselective protection and deprotection of myo-inositol provided azide 43 as key intermediate. In the final steps deprotection of five benzyl groups and reduction of azido group was achieved by catalytic hydrogenation. scyllo-Inosamine hydrochloride 6 was fully characterized by m.p., ¹H NMR, ¹³C NMR, IR, EA and via its acetate derivative. Moreover we investigated the bacterial oxidation of myo-inositol 23, the Swem oxidation of diol 35, and the reduction of oxime 2.

Recommended Citation

Gurung, Sing Raj, "Synthesis and Characterization of Inosamines" (2006). Masters Theses. 4329.
https://scholarworks.wmich.edu/masters_theses/4329