An iterative cross-coupling based approach to the synthesis of peridinin and progress towards peridinin derivatives
Davis, Erin
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https://hdl.handle.net/2142/45557
Description
Title
An iterative cross-coupling based approach to the synthesis of peridinin and progress towards peridinin derivatives
Author(s)
Davis, Erin
Issue Date
2013-08-22T16:47:44Z
Director of Research (if dissertation) or Advisor (if thesis)
Burke, Martin D.
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
M.S.
Degree Level
Thesis
Keyword(s)
peridinin
lipoperoxidation
carotenoids
iterative cross coupling
Abstract
Lipoperoxidation plays a role in diseases such as atherosclerosis, rheumatoid arthritis, cancer, and may contribute to the general phenomenon of aging. As individuals with deficiencies of antioxidant proteins are particularly susceptible to these diseases, small molecules with the ability to act as antilipoperoxidants have the potential to serve as powerful pharmaceuticals. Peridinin, an atypical carotenoid found in dinoflagellates responsible for the color of red tide, is especially interesting as a potential antilipoperoxidant because it may act through self-preserving mechanisms, unlike other carotenoids. We report the total synthesis of the protected form of a peridinin derivative lacking the butenolide functionality and contributions towards the development of a stereoretentive Suzuki-Miyaura coupling of haloallenes.
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