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

被引：6
|
作者：
Ocampo, Charles E. [1 ]
Lee, Doris [1 ]
Jamison, Timothy F. [1 ]
机构：
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 04期
基金：
加拿大自然科学与工程研究理事会;
关键词：
ENANTIOMERIC N-(2-PHOSPHONOMETHOXYPROPYL) DERIVATIVES; PYRIMIDINE-BASES; PHOSPHONATE; PURINE; ANALOGS; PMPA; HIV;
D O I：
10.1021/ol503612h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：820 / 823
页数：4
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