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Title page for ETD etd-10292014-131457

Type of Document Master's Thesis
Author Berry, Cynthia Gayle Bollinger
URN etd-10292014-131457
Title Progress toward the Total Synthesis of Marineosin A and the Synthesis and Optimization of a Selective Dopamine Receptor 4 Antagonist for Use as a PET Tracer and an in vivo Tool to Study Cocaine Addiction
Degree Master of Science
Department Chemistry
Advisory Committee
Advisor Name Title
Craig W. Lindsley Committee Chair
Gary A. Sulikowski Committee Member
  • D4
  • marineosin
Date of Defense 2014-10-24
Availability unrestricted
Marineosin A is a biologically active natural product with a novel and complex structure. Many attempts to synthesize marineosin A without success have been reported. The Lindsley lab has completed a 21-step synthesis to an advanced intermediate containing most of the carbon backbone and four of the five stereocenters of marineosin A. In addition, two model systems have been used to study the proposed final transformations needed to complete the total synthesis.

The synthesis of highly selective ligands for the five dopamine receptor subtypes has remained challenging, and the lack of such ligands for the dopamine 4 receptor (D4) has limited our knowledge of its function. The Lindsley lab has begun a structure-activity relationship study of a novel D4 antagonist from which a highly selective and potent compound has been identified. This molecule was shown to reduce cocaine-induced hyperlocomotion in rats and will be further used to study cocaine addiction and the possible role D4 plays in this disease.

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