Gold Catalyzed Lactonization of Epoxide Esters
Research Mentor(s)
Vyvyan, James R.
Description
Lactones are cyclic esters of varying ring size that occur naturally in organic compounds. Organic structures such as these have various useful biological activities applicable to antibacterial drugs, potential anticancer drugs, and participants of metabolic processes. Gold catalysts Au(I) and Au(III) are shown in our experiments to be effective in inducing intramolecular lactonization of epoxide esters to form desired lactone products. In our experiments gold catalysts coordinated with epoxides to develop a positive charge on the carbon nearest to the carbonyl. The result is an intramolecular lactonization of the ester via nucleophilic attack of the carbonyl oxygen onto the positive carbon of the epoxide. Through these methods we may be able to further our experiments to develop more complex lactones like those seen in biologically relevant compounds.
Document Type
Event
Start Date
19-5-2016 12:00 PM
End Date
19-5-2016 3:00 PM
Department
Chemistry
Genre/Form
student projects; posters
Subjects – Topical (LCSH)
Organogold compounds; Gold; Catalysts
Type
Image
Keywords
Gold, Catalysis, Organogold, Epoxide, Lactone, Esters
Rights
Copying of this document in whole or in part is allowable only for scholarly purposes. It is understood, however, that any copying or publication of this documentation for commercial purposes, or for financial gain, shall not be allowed without the author's written permission.
Language
English
Format
application/pdf
Gold Catalyzed Lactonization of Epoxide Esters
Lactones are cyclic esters of varying ring size that occur naturally in organic compounds. Organic structures such as these have various useful biological activities applicable to antibacterial drugs, potential anticancer drugs, and participants of metabolic processes. Gold catalysts Au(I) and Au(III) are shown in our experiments to be effective in inducing intramolecular lactonization of epoxide esters to form desired lactone products. In our experiments gold catalysts coordinated with epoxides to develop a positive charge on the carbon nearest to the carbonyl. The result is an intramolecular lactonization of the ester via nucleophilic attack of the carbonyl oxygen onto the positive carbon of the epoxide. Through these methods we may be able to further our experiments to develop more complex lactones like those seen in biologically relevant compounds.