Date of Thesis

Spring 2024

Description

Bile acids are biological surfactants normally found in the digestive system

of humans and other organisms. They have many biological importance such as

regulating lipid digestion and glucose metabolism. In addition to their biological

importance, they also have the potential to aggregate together to form micelles,

this micelle formation makes them useful in drug delivery and chiral separation.

Homo bile acids have one or two carbon extensions at the C17 side chain, similar

to the normal bile acids, the homo bile acids also have very important biological

functions and also have the potential to enhance chiral separation and selectivity.

Within this thesis, we have discussed several approaches toward the synthesis of

homo-bile acids.

Although the previous approaches towards these homo bile acids gave

some good yield, most involved protection of the C3, C7, and C12 hydroxyl groups

before functionalizing the C24 position. This protecting group chemistry adds

additional steps to the overall reaction sequence due to the introduction and

cleavage of protecting groups.

The focus within our lab was to minimize the use of

protecting groups by employing a selective functionalization strategy to synthesize

these homo bile acids with an improved overall yield. This selective

functionalization strategy was successfully implemented for the synthesis of C25

homo and C26 bishomo bile acids with an improved yield compared to literature

reports and starting with commercially available bile acids.

Keywords

Bile acid, Mitsunobu, regioselective, selective functionalization, homologation, homo bile acids.

Access Type

Masters Thesis (Bucknell Access Only)

Degree Type

Master of Science

Major

Chemistry

First Advisor

Michael Krout

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