Synthetic studies towards trichodermamide B: expedient synthesis enabled by arene oxide equivalents
Reynolds, Bryan Joseph
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https://hdl.handle.net/2142/89043
Description
Title
Synthetic studies towards trichodermamide B: expedient synthesis enabled by arene oxide equivalents
Author(s)
Reynolds, Bryan Joseph
Issue Date
2015-12-04
Director of Research (if dissertation) or Advisor (if thesis)
Sarlah, David
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
M.S.
Degree Level
Thesis
Keyword(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.
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