Novel methods and syntheses toward HIV/AIDS and tuberculosis pharmaceuticals
Author(s)Ocampo, Charles E. (Charles Edward)
Massachusetts Institute of Technology. Department of Chemistry.
Timothy F. Jamison.
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[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.
Thesis: Ph. D. in Organic Chemistry, Massachusetts Institute of Technology, Department of Chemistry, 2017.Cataloged from PDF version of thesis.Includes bibliographical references.
DepartmentMassachusetts Institute of Technology. Department of Chemistry.; Massachusetts Institute of Technology. Department of Chemistry
Massachusetts Institute of Technology