An iterative cross-coupling based approach to the synthesis of peridinin and progress towards peridinin derivatives

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.

Name thesis:degree_name

M.S.

Level thesis:degree_level

Thesis

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2013

Author dc:creator

• Davis, Erin

Contributors dc:contributor

• Burke, Martin D.

• peridinin
• lipoperoxidation
• carotenoids
• iterative cross coupling

Statement dc:rights

• Copyright 2013 Erin Davis

Language dc:language

en

Handle dc:identifier

http://hdl.handle.net/2142/45557

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/45557