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

Author(s)
Ocampo, Charles Edward; Lee, Doris; Jamison, Timothy F
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Abstract
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.
Date issued
2015-02
URI
http://hdl.handle.net/1721.1/105334
Department
Massachusetts Institute of Technology. Department of Chemistry
Journal
Organic Letters
Publisher
American Chemical Society (ACS)
Citation
Ocampo, Charles E., Doris Lee, and Timothy F. Jamison. “Selective Lewis Acid Catalyzed Assembly of Phosphonomethyl Ethers: Three-Step Synthesis of Tenofovir.” Organic Letters 17, no. 4 (February 20, 2015): 820-823.
Version: Author's final manuscript
ISSN
1523-7060
1523-7052
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