Synthesis of α-Fluorinated Phosphonates from α-Fluorovinylphosphonates: A New Route to Analogues of Lysophosphatidic Acid
- 31 May 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (13), 2267-2270
- https://doi.org/10.1021/ol034597+
Abstract
A versatile, efficient method for the preparation of α-monofluoromethylene (−CHF−) phosphonates from α-fluorovinylphosphonate provides access to a class of lysophosphatidic acid (LPA) receptor-subtype agonists. In addition, sn-2 O-methylation of α-monofluoromethylene phosphonates using trimethylsilyldiazomethane generated sn-1-acyl, 2-O-methyl α-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 α-monofluoromethylene LPA analogues was prepared.Keywords
This publication has 9 references indexed in Scilit:
- Identification of a Phosphothionate Analogue of Lysophosphatidic Acid (LPA) as a Selective Agonist of the LPA3 ReceptorJournal of Biological Chemistry, 2003
- Identification of an intracellular receptor for lysophosphatidic acid (LPA): LPA is a transcellular PPARγ agonistProceedings of the National Academy of Sciences, 2002
- (α-Monofluoroalkyl)phosphonates: a class of isoacidic and “tunable” mimics of biological phosphatesJournal of Fluorine Chemistry, 2001
- A Convergent Triflate Displacement Approach to (α-Monofluoroalkyl)phosphonatesOrganic Letters, 2001
- Bioactive Lysophospholipids and Their G Protein-Coupled ReceptorsExperimental Cell Research, 1999
- Synthesis of monofluoro- and difluoro- methylenephosphonate analogues of sn-glycerol-3-phosphate as substrates for glycerol-3-phosphate dehydrogenase and the X-ray structure of the fluoromethylenephosphonate moietyTetrahedron, 1996
- Fluorinated retinoic acids and their analogs. 3. Synthesis and biological activity of aromatic 6-fluoro analogsJournal of Medicinal Chemistry, 1982
- Unsaturated carbenes from primary vinyl triflates. 6. Competitive addition of isopropylidenecarbene to olefinsThe Journal of Organic Chemistry, 1977
- Absolute configuration of substituted trifluoromethylcarbinolsThe Journal of Organic Chemistry, 1968