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  • Title: Synthesis of alpha-fluorinated phosphonates from alpha-fluorovinylphosphonates: a new route to analogues of lysophosphatidic acid.
    Author: Xu Y, Qian L, Prestwich GD.
    Journal: Org Lett; 2003 Jun 26; 5(13):2267-70. PubMed ID: 12816425.
    Abstract:
    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 trimethylsilyldiazomethane 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. [reaction: see text]
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