Date of Award
4-2005
Degree Name
Master of Science
Department
Chemistry
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
Abstract
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.
Recommended Citation
Guduru, Venkat Reddy, "Rhizopine Synthesis – Potential Mediators for Nitrogen Fixation in Legume Plants" (2005). Masters Theses. 4556.
https://scholarworks.wmich.edu/masters_theses/4556