Synthetic studies towards trichodermamide B: expedient synthesis enabled by arene oxide equivalents

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.

Name thesis:degree_name

M.S.

Level thesis:degree_level

Thesis

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2016

Author dc:creator

• Reynolds, Bryan Joseph

Contributors dc:contributor

• Sarlah, David

• Trichodermamide B
• arene oxide
• dearomatization
• alkylation
• natural product
• total synthesis
• biomimetic

Statement dc:rights

• Copyright 2015 Bryan Reynolds

Language dc:language

en

Handle dc:identifier

http://hdl.handle.net/2142/89043

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/89043