Department or Program

Chemistry

Abstract

Plants used in traditional medicine are often studied in order to isolate natural products for the development of modern pharmaceuticals. One plant which has recently begun to be studied in relation to its pharmacological properties is Lindera fruticosa. L. fruticosa is a green shrub which has historically been used in Southeast Asia as a remedy for gastric trouble and other ailments. Linderofruticoside A is a novel phenolic glycoside isolated from L. fruticosa which contains unique structural elements that show promise for use in pharmaceuticals. The unique structure of linderofruticoside A includes an unusual 13-membered lactone, a disaccharide formed from D-apiose and D-xylose, and a phenolic glycoside derived from gentisic acid. Due to the limited amount of linderofruticoside A which can be isolated from L. fruticosa, a full synthesis is required to study its properties. Two different synthetic pathways combining glycosylation and esterification reactions are described here. Each pathway utilizes the three compounds stated above as starting materials. Thus far, multiple derivatives of xylose, apiose, and gentisic acid have been synthesized to develop and refine protecting schemes for each compound. Additionally, the β-O-glycosidic bond has successfully been formed between xylose and gentisic acid.

Level of Access

Restricted: Campus/Bates Community Only Access

First Advisor

Koviach-Cote, Jennifer

Date of Graduation

5-2020

Degree Name

Bachelor of Science

Number of Pages

57

Components of Thesis

1 pdf file

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