Selective Lewis Acid Catalyzed Assembly of Phosphonomethyl Ethers: Three-Step Synthesis of Tenofovir

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...

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Bibliographic Details
Main Authors: Ocampo, Charles Edward (Contributor), Lee, Doris (Contributor), Jamison, Timothy F (Contributor)
Other Authors: Massachusetts Institute of Technology. Department of Chemistry (Contributor)
Format: Article
Language:English
Published: American Chemical Society (ACS), 2016-11-15T20:00:07Z.
Subjects:
Online Access:Get fulltext
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042 |a dc 
100 1 0 |a Ocampo, Charles Edward  |e author 
100 1 0 |a Massachusetts Institute of Technology. Department of Chemistry  |e contributor 
100 1 0 |a Jamison, Timothy F  |e contributor 
100 1 0 |a Ocampo, Charles Edward  |e contributor 
100 1 0 |a Lee, Doris  |e contributor 
100 1 0 |a Jamison, Timothy F  |e contributor 
700 1 0 |a Lee, Doris  |e author 
700 1 0 |a Jamison, Timothy F  |e author 
245 0 0 |a Selective Lewis Acid Catalyzed Assembly of Phosphonomethyl Ethers: Three-Step Synthesis of Tenofovir 
260 |b American Chemical Society (ACS),   |c 2016-11-15T20:00:07Z. 
856 |z Get fulltext  |u http://hdl.handle.net/1721.1/105334 
520 |a 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. 
520 |a Bill & Melinda Gates Foundation ("Medicines for All" Initiative) 
520 |a Natural Sciences and Engineering Research Council of Canada (NSERC Postdoctoral Fellowship) 
546 |a en_US 
655 7 |a Article 
773 |t Organic Letters