Access Type
Open Access Dissertation
Date of Award
January 2023
Degree Type
Dissertation
Degree Name
Ph.D.
Department
Chemistry
First Advisor
Jennifer L. Stockdill
Abstract
This thesis primarily focuses on synthesizing fragments of microcystin-LR, which is a natural product, with the aim of establishing them as analytical standards for investigating the biodegradation pathways of MC-LR. Despite of the substantial interest in synthesizing, isolating, and degrading Microcystins over the past few decades, the availability of high-purity microcystin standards at known concentration for quantitative analysis of using LC-MS/MS remains limited. The synthesis of the proposed MC-LR fragments employs the Fmoc/t-Bu protecting group strategy to prevent isomerization. Additionally, novel methods for the total synthesis of N-Boc-Adda are explored, incorporating atom-economic approaches, cross-metathesis, and oxidative boron Heck reactions. The research highlights the utilization of selective reaction such as hydrosilylatiion, enyne metathesis, hydrohydroxylalkylation, olefin cross-metathesis, Evans aldol addition, Horner-Emmons Wadsworth, and Mitsunobu reactions. Moreover, an Oscillamide Y analog is synthesized bidirectionally (C to N and N to C) by utilizing an N-acyl urea functionality in conjunction with the ε-Lys sidechain, resulting in the formation of macrocycle.
Recommended Citation
Yadab, Mahesh Kumar, "Synthesis Of Putative Microcystin-Lr Degradation Products And Full Macrocyclic Cyanopeptide" (2023). Wayne State University Dissertations. 3917.
https://digitalcommons.wayne.edu/oa_dissertations/3917