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Studies Toward the Total Synthesis of Tetrahydrofuran-Containing Natural Products

Resource type
Thesis type
(Thesis) M.Sc.
Date created
2016-07-14
Authors/Contributors
Author: Kwon, Daniel
Abstract
Natural products have played a significant role as leads and inspiration for many novel therapeutics. Among the most common structural fragments found in biologically active natural products is the tetrahydrofuran, a five membered oxygen-containing heterocycle. As oftentimes very little natural product is available from the producing organism, there has been a longstanding interest in the development of efficient and general synthetic methods to access tetrahydrofurans and tetrahydrofuran-containing natural products. This thesis summarizes recent efforts directed towards the total synthesis of amphirionin-4 and biselide A, two tetrahydrofuran-containing natural products with potentially useful biological activities. Amphirionin-4 is a polyketide isolated from Amphidinium sp. dinoflagellates, and has demonstrated potent proliferation activity in ST-2 stem cells. Biselide A is a marine macrolide isolated from the Okinawan ascidian Didemnidae sp., and has demonstrated potent cytotoxicity towards a variety of human cancer cell lines. Notably, the unifying element in our synthetic approaches to both of these natural products is a reliance on chlorohydrin-based strategies to access the tetrahydrofuran cores in an efficient, diastereoselective and enantioselective manner.
Document
Identifier
etd9655
Copyright statement
Copyright is held by the author.
Permissions
This thesis may be printed or downloaded for non-commercial research and scholarly purposes.
Scholarly level
Supervisor or Senior Supervisor
Thesis advisor: Britton, Robert A.
Member of collection
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etd9655_DKwon.pdf 3.42 MB

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