Novel methods and syntheses toward HIV/AIDS and tuberculosis pharmaceuticals
Name
1008887321-MIT.pdf
Description
Full printable version
Size
13.36 MB
Format
Adobe PDF
Checksum (MD5)
4c07fe925f1a01ff2fbed637fcfac0ff
Author(s)
Ocampo, Charles E. (Charles Edward)
Advisor(s)
Timothy F. Jamison.
Date Issued
2017
Publisher
Massachusetts Institute of Technology
Abstract
[chemical formula] Described herein is a novel Lewis acid catalyzed rearrangement-coupling of oxygen heterocycles and bis(diethylamino)chlorophosphine that provides direct formation of the phosphonomethyl ether functionality found in several important antiretroviral agents. A wide range of dioxolanes and 1,3-dioxanes may be employed, furnishing the desired products in good yield. The utility of this method is demonstrated in a novel synthesis of tenofovir, an antiretroviral drug used in the treatment of HIV/AIDS and hepatitis B. [chemical formula] We have proposed a novel synthesis toward bedaquiline, the latest pharmaceutical to be released in the market for the treatment of multi-drug resistant tuberculosis. The synthesis of the final epoxide intermediate of our route has been achieved on multi-gram scale, and the subject of future investigation will focus on the final epoxide opening reaction. Our proposed route uses readily available, inexpensive starting materials, and would afford bedaquiline in a convergent fashion requiring six steps.
Description
Thesis: Ph. D. in Organic Chemistry, Massachusetts Institute of Technology, Department of Chemistry, 2017.
Cataloged from PDF version of thesis.
Includes bibliographical references.
Subjects
Chemistry.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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