Efforts toward the total synthesis of premnalatifolin A and martinelline

Date
2025
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Publisher
University of Delaware
Abstract
This thesis focuses on the efforts toward the total synthesis of two complex natural products: premnalatifolin A and martinelline and my related works are described in detail in the chapters within. ☐ Premnalatifolin A is an icetexane natural products with a wide array of biological activities and interesting structural features. Chapter one builds upon in greater detail a published review from 2022 in the Chain group, highlighting classifications of icetexanes, recent isolations, and highlighted synthetic routes toward icetexanes. ☐ Chapter two outlines our initial synthetic efforts on synthesis of premnalatifolin A, a potent potential breast cancer and colon cancer therapeutic. Gathering inspiration from the published works of Mr. Moon and Dr. Al–Amin we generated both a TBS and trimethoxy protected southern monomers of premnalatifolin A. ☐ Chapter three highlights our second-generation synthesis premnalatifolin A, utilizing an electrochemically enabled pyridinium sp2-sp3 cross coupling recently developed in the laboratories of Dr. Mary Watson. Additionally, chapter three outlines a novel medicinal chemistry approach to accessing a large variety of synthetic analogs of icetexanes for therapeutic development. ☐ Chapter four investigates the Chain groups efforts to apply tandem Polovnoski– Povarov methodology developed in the laboratory to leverage aniline N-oxides towards the total synthesis of the complex tetrahydroquinoline alkaloid martinelline and other related natural products.
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Keywords
Premnalatifolin A, Martinelline, Breast cancer
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