Honors Capstone Project
Date of Submission
Arts and Science
Capstone Prize Winner
Won Capstone Funding
Sciences and Engineering
The goal of this study is the synthesis of centrolobine 7, a naturally-occuring compound that exhibits anti-parasitic and anti-inflammatory activity.
The strategy is to utilize the carbonyl ene reaction to form the 2,6-disubstituted framework of centrolobine 7 from exocyclic enol ether 110 and aldehyde 111. Exocyclic enol ether 110 would be synthesized via literature procedures starting from commercially available glutaric anhydride 11 and anisole 114.
The work completed to date optimizing the following reactions: Friedel-Crafts acylation of glutaric anhydride 11 and anisole 114, the reduction of alcohol 116, and cyclization of alcohol 116 to lactone 112. To form exocyclic enol ether 110 from lactone 112. Difficulties with isomerization to the corresponding endocyclic enol ether 126 prevented an optimized converstion of lactone 112 to exocyclic enol ether 110. The ene reaction of exocyclic enol ether 110 and aldehyde 111 showed some promise. Significant progress was made towards the synthesis of centrolobine 7 via the carbonyl ene reaction, and can be completed in future studies.
Shores, Brianna, "Studies towards the synthesis of (-)-centrolobine via the carbonyl ene reaction of exocyclic enol ethers" (2017). Syracuse University Honors Program Capstone Projects. 1019.
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