Degree Type
Honors Capstone Project
Date of Submission
Spring 5-2017
Capstone Advisor
Nancy Totah
Honors Reader
James Kallmerten
Capstone Major
Chemistry
Capstone College
Arts and Science
Audio/Visual Component
no
Capstone Prize Winner
no
Won Capstone Funding
no
Honors Categories
Sciences and Engineering
Subject Categories
Chemistry
Abstract
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.
Recommended Citation
Shores, Brianna, "Studies towards the synthesis of (-)-centrolobine via the carbonyl ene reaction of exocyclic enol ethers" (2017). Honors Capstone Projects - All. 1019.
https://surface.syr.edu/honors_capstone/1019
Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License.
