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.

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