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.
","abstract_html":"<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>","abstract_has_math":false,"creators":["Abou Aleiwi, Bilal"],"institution":null,"degree_name":"Ph.D.","degree_level":"Open Access Dissertation","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["JAMES H. RIGBY"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2010,"date_issued":"2010-01-01T08:00:00Z","date_published":"2010-01-01T08:00:00Z","updated_at":"2026-07-24T05:58:42Z","subjects":["HIGHER ORDER CYCLOADDITION REACTIONS","Organic Chemistry"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://digitalcommons.wayne.edu/oa_dissertations/136","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["JAMES H. RIGBY"]},{"key":"dc:creator","label":"Author","values":["Abou Aleiwi, Bilal"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.available","label":"Dc Date Available","values":["2010-11-08T08:00:00Z"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Open Access Dissertation"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Ph.D."]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["HIGHER ORDER CYCLOADDITION REACTIONS","Organic Chemistry"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://digitalcommons.wayne.edu/oa_dissertations/136"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["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.
"]},{"key":"dc:title","label":"Title","values":["Transition Metal-Mediated Higher-Order Cycloaddition Reactions: Application To The Total Synthesis Of Complex Natural Products"]}]}],"canonical_facts":{"dc:contributor":["JAMES H. RIGBY"],"dc:creator":["Abou Aleiwi, Bilal"],"dc:date.available":["2010-11-08T08:00:00Z"],"dc:description.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.
"],"dc:identifier":["https://digitalcommons.wayne.edu/oa_dissertations/136"],"dc:subject":["HIGHER ORDER CYCLOADDITION REACTIONS","Organic Chemistry"],"dc:title":["Transition Metal-Mediated Higher-Order Cycloaddition Reactions: Application To The Total Synthesis Of Complex Natural Products"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Open Access Dissertation"],"thesis:degree_name":["Ph.D."]},"updated_at":"2026-07-24T05:58:42Z"}