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Title:Synthetic studies towards trichodermamide B: expedient synthesis enabled by arene oxide equivalents
Author(s):Reynolds, Bryan Joseph
Advisor(s):Sarlah, David
Department / Program:Chemistry
Discipline:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Degree:M.S.
Genre:Thesis
Subject(s):Trichodermamide B
arene oxide
dearomatization
alkylation
natural product
total synthesis
biomimetic
Abstract:Trichodermamide B, isolated from the marine fungus Trichoderma virens in 2003, is a potent anti-cancer agent and with complex molecular architecture. It is hypothesized herein that this molecule may be derived in nature from phenylalanine via a benzene oxide intermediate. Utilizing a bioinspired strategy, synthetic studies towards trichodermamide B have been conducted utilizing arene oxide equivalents as key synthetic intermediates. Notable synthetic transformations include alkylation with a novel, α–bromo oximoester electrophile and allylic bromination of an advanced, spirocyclic intermediate. This strategy has enabled access to advanced intermediates and should afford the natural product in far fewer steps than previously reported syntheses of this compound. Once complete, this concise synthetic strategy should afford enough material to conduct mechanism of action studies to uncover the origin of trichodermamide B’s impressive biological activity.
Issue Date:2015-12-04
Type:Thesis
URI:http://hdl.handle.net/2142/89043
Rights Information:Copyright 2015 Bryan Reynolds
Date Available in IDEALS:2016-03-02
Date Deposited:2015-12


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