Synthesis of α-fluorinated phosphonates from α-fluorovinylphosphonates:: A new route to analogues of lysophosphatidic acid

被引：58
|
作者：
Xu, Y [1 ]
Qian, L [1 ]
Prestwich, GD [1 ]
机构：
[1] Univ Utah, Dept Med Chem, Salt Lake City, UT 84108 USA
来源：
ORGANIC LETTERS | 2003年 / 5卷 / 13期
关键词：
D O I：
10.1021/ol034597+
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A versatile, efficient method for the preparation of alpha-monofluoromethylene (-CHF-) phosphonates; from alpha-fluorovinylphosphonate provides access to a class of lysophosphatidic acid (LPA) receptor-subtype agonists. In addition, sn-2 O-methylation of alpha-monofluoromethylene phosphonates using trimethylsilyidiazomethane generated sn-1-acyl, 2-O-methyl alpha-monofluoromethylene derivatives. Finally, a novel method for the selective etherification of 1,2-diols was developed and a new class of sn-1 O-methyl, 2-acyl alpha-monofluoromethylene LPA analogues was prepared.
引用
收藏
页码：2267 / 2270
页数：4
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