Date of Award


Degree Name

Master of Science



First Advisor

Dr. Elke Schoffers

Second Advisor

Dr. Subra Muralidharan

Third Advisor

Dr. James Kiddle

Fourth Advisor

Dr. Silvia Rossbach

Access Setting

Masters Thesis-Open Access


This research project focused on novel and efficient synthetic approaches of inosamine derivatives (rhizopines). The preparation of specific rhizopines would help elucidate the microbial pathway of rhizopine catabolism and degradation, and determine the role of corresponding genes during nitrogen fixation. We have investigated regio - and stereoselective transformations of myo-inositol derivative 28 utilizing an organostannane as key intermediate towards rhizopine 1a. The synthesis involved several protection and deprotection strategies to control competing reactivities of six hydroxyl groups of myo-inositol. Rhizopine 1a was prepared efficiently as a single isomer in 8 steps and 13% yield by controlling reactions regio - and stereoselectively.

Included in

Chemistry Commons