Transition Metal-Mediated Higher-Order Cycloaddition Reactions: Application To The Total Synthesis Of Complex Natural Products

<p>ABSTRACT</p> <p>TRANSITION METAL-MEDIATED HIGHER-ORDER CYCLOADDITION REACTIONS: APPLICATION TO THE TOTAL SYNTHESIS OF COMPLEX NATURAL PRODUCTS</p> <p>by</p> <p>BILAL ABOU ALEIWI</p> <p>October 2010</p> <p>Advisor: Dr. James H. Rigby</p> <p>Major: Chemistry (Organic)</p> <p>Degree: Doctor of Philosophy</p> <p>Chromium (0)-mediated [6ð + 2ð] and [6ð + 2ð + 2ð] cycloaddition reactions between cyclic trienes and alkynes is reported. The development, investigation and the application of these reactions in the total synthesis of complex ring systems and natural products is described. Two natural products, namely, ∆ 9(12) -Capnellene and Echinopines A and B were targeted.</p> <p>An investigation led to the successful development of a methodology to form the linear triquinane ring system of the natural product ∆ 9(12) -Capnellene. This methodology relies mainly on a tandem Chromium (0)-mediated [6ð + 2ð] cycloaddition reaction and a radical cyclization reaction.</p>

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Open Access Dissertation

Discipline thesis:degree_discipline

Chemistry

Year dc:date.available

2010

Author dc:creator

• Abou Aleiwi, Bilal

Contributors dc:contributor

• JAMES H. RIGBY

• HIGHER ORDER CYCLOADDITION REACTIONS
• Organic Chemistry

Repository record dc:identifier

https://digitalcommons.wayne.edu/oa_dissertations/136

OAI identifier oai:identifier

oai:digitalcommons.wayne.edu:oa_dissertations-1135