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-dioxa...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2015-02, Vol.17 (4), p.820-823
Hauptverfasser: Ocampo, Charles E, Lee, Doris, Jamison, Timothy F
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol503612h