{"id":{"repo_id":"mit","oai_identifier":"oai:dspace.mit.edu:1721.1/112441"},"canonical_url":"https://search.dev.ndltd.org/etd/mit/oai:dspace.mit.edu:1721.1/112441","repository":{"repo_id":"mit","name":"MIT","base_url":"https://dspace.mit.edu/oai/request"},"display":{"title":"Novel methods and syntheses toward HIV/AIDS and tuberculosis pharmaceuticals","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.","abstract_html":"[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.","abstract_has_math":false,"creators":["Ocampo, Charles E. (Charles Edward)"],"institution":"Massachusetts Institute of Technology","degree_name":null,"degree_level":null,"degree_discipline":null,"degree_department":"Massachusetts Institute of Technology. Department of Chemistry.","school":null,"contributors":[],"advisors":["Timothy F. Jamison."],"committee_chairs":[],"committee_members":[],"year":2017,"date_issued":"2017","date_published":"2017","updated_at":"2026-07-22T22:20:54Z","subjects":["Chemistry."],"languages":["eng"],"rights":["MIT theses are protected by copyright. They may be viewed, downloaded, or printed from this source but further reproduction or distribution in any format is prohibited without written permission."],"rights_urls":["http://dspace.mit.edu/handle/1721.1/7582"],"identifier_entries":[]},"links":{"outbound_url":"http://hdl.handle.net/1721.1/112441","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.advisor","label":"Advisor","values":["Timothy F. Jamison."]},{"key":"dc:contributor.department","label":"Department","values":["Massachusetts Institute of Technology. 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They may be viewed, downloaded, or printed from this source but further reproduction or distribution in any format is prohibited without written permission."]},{"key":"dc:rights.uri","label":"Rights URI","values":["http://dspace.mit.edu/handle/1721.1/7582"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["http://hdl.handle.net/1721.1/112441"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["Thesis: Ph. D. in Organic Chemistry, Massachusetts Institute of Technology, Department of Chemistry, 2017.","Cataloged from PDF version of thesis.","Includes bibliographical references."]},{"key":"dc:description.abstract","label":"Abstract","values":["[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."]},{"key":"dc:description.degree","label":"Dc Description Degree","values":["Ph. D. in Organic Chemistry"]},{"key":"dc:title","label":"Title","values":["Novel methods and syntheses toward HIV/AIDS and tuberculosis pharmaceuticals"]}]}],"canonical_facts":{"dc:contributor.advisor":["Timothy F. Jamison."],"dc:contributor.department":["Massachusetts Institute of Technology. Department of Chemistry."],"dc:contributor.other":["Massachusetts Institute of Technology. Department of Chemistry."],"dc:creator":["Ocampo, Charles E. (Charles Edward)"],"dc:date.accessioned":["2017-12-05T19:12:56Z"],"dc:date.available":["2017-12-05T19:12:56Z"],"dc:date.issued":["2017"],"dc:description":["Thesis: Ph. D. in Organic Chemistry, Massachusetts Institute of Technology, Department of Chemistry, 2017.","Cataloged from PDF version of thesis.","Includes bibliographical references."],"dc:description.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."],"dc:description.degree":["Ph. D. in Organic Chemistry"],"dc:identifier.uri":["http://hdl.handle.net/1721.1/112441"],"dc:language.iso":["eng"],"dc:publisher":["Massachusetts Institute of Technology"],"dc:rights":["MIT theses are protected by copyright. They may be viewed, downloaded, or printed from this source but further reproduction or distribution in any format is prohibited without written permission."],"dc:rights.uri":["http://dspace.mit.edu/handle/1721.1/7582"],"dc:subject":["Chemistry."],"dc:title":["Novel methods and syntheses toward HIV/AIDS and tuberculosis pharmaceuticals"],"dc:type":["Thesis"]},"updated_at":"2026-07-22T22:20:54Z"}