Access Type
Open Access Dissertation
Date of Award
1-1-2010
Degree Type
Dissertation
Degree Name
Ph.D.
Department
Chemistry
First Advisor
JAMES H. RIGBY
Abstract
ABSTRACT
TRANSITION METAL-MEDIATED HIGHER-ORDER CYCLOADDITION REACTIONS: APPLICATION TO THE TOTAL SYNTHESIS OF COMPLEX NATURAL PRODUCTS
by
BILAL ABOU ALEIWI
October 2010
Advisor: Dr. James H. Rigby
Major: Chemistry (Organic)
Degree: Doctor of Philosophy
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.
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.
Recommended Citation
Abou Aleiwi, Bilal, "Transition Metal-Mediated Higher-Order Cycloaddition Reactions: Application To The Total Synthesis Of Complex Natural Products" (2010). Wayne State University Dissertations. 136.
https://digitalcommons.wayne.edu/oa_dissertations/136