Open Access Dissertation
Date of Award
JAMES H. RIGBY
TRANSITION METAL-MEDIATED HIGHER-ORDER CYCLOADDITION REACTIONS: APPLICATION TO THE TOTAL SYNTHESIS OF COMPLEX NATURAL PRODUCTS
BILAL ABOU ALEIWI
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.
Abou Aleiwi, Bilal, "Transition Metal-Mediated Higher-Order Cycloaddition Reactions: Application To The Total Synthesis Of Complex Natural Products" (2010). Wayne State University Dissertations. Paper 136.