Synthesis of alpha-fluorinated phosphonates from alpha-fluorovinylphosphonates: a new route to analogues of lysophosphatidic acid.
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]
Xu
Yong
Y
Department of Medicinal Chemistry, The University of Utah, 419 Wakara Way, Suite 205, Salt Lake City, UT 84108-1257, USA.
Qian
Lian
L
Prestwich
Glenn D
GD
D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis / Q000737:chemistry*; D008246:Lysophospholipids / Q000138:chemical synthesis* / Q000737:chemistry*; D008745:Methylation; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
D006845:Hydrocarbons, Fluorinated; D008246:Lysophospholipids; D063065:Organophosphonates; D014753:Vinyl Compounds