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
相关论文
共 50 条
  • [1] Synthesis of α-fluorinated phosphonates as metabolically stabilized lysophosphatidic acid analogues
    Xu, Y
    Prestwich, GD
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 227 : U190 - U190
  • [2] Structure-activity relationships of fluorinated lysophosphatidic acid analogues
    Xu, Y
    Aoki, J
    Shimizu, K
    Umezu-Goto, M
    Hama, K
    Takanezawa, Y
    Yu, SX
    Mills, GB
    Arai, H
    Qian, L
    Prestwich, GD
    JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (09) : 3319 - 3327
  • [3] Synthesis of monofluorinated analogues of lysophosphatidic acid
    Xu, Y
    Qian, L
    Prestwich, GD
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (13): : 5320 - +
  • [4] Synthesis of difluoromethyl substituted lysophosphatidic acid analogues
    Xu, Y
    Qian, L
    Pontsler, AV
    McIntyre, TM
    Prestwich, GD
    TETRAHEDRON, 2004, 60 (01) : 43 - 49
  • [5] VINYL PHOSPHONATES - A CONVENIENT ROUTE TO PHOSPHONIC ACID ANALOGUES OF PHOSPHATE MONOESTERS
    HULLAR, TL
    TETRAHEDRON LETTERS, 1967, (49) : 4921 - &
  • [6] An Efficient Synthesis of (±)-Trichostatic Acid and Analogues: A New Route to (±)-Trichostatin A
    Chatterjee, Anamitra
    Richer, Joshua
    Hulett, Tyler
    Iska, Vijaya Bhaskara Reddy
    Wiest, Olaf
    Helquist, Paul
    ORGANIC LETTERS, 2010, 12 (04) : 832 - 834
  • [7] Synthesis and biological evaluation of metabolically stabilized lysophosphatidic acid analogues
    Prestwich, GD
    Xu, Y
    Qian, L
    Hama, K
    Aoki, J
    FASEB JOURNAL, 2003, 17 (05): : A994 - A994
  • [8] Synthesis of migration-resistant hydroxyethoxy analogues of lysophosphatidic acid
    Qian, L
    Xu, Y
    Arai, H
    Aoki, J
    McIntyre, TM
    Prestwich, GD
    ORGANIC LETTERS, 2003, 5 (24) : 4685 - 4688
  • [9] The synthesis of new fluorinated or nonfluorinated sugar phosphonates and phosphoramidates as building blocks in the synthesis of modified hyaluronic acid subunits
    Koroniak-Szejn, Katarzyna
    Tomaszewska, Joanna
    Koroniak, Henryk
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2017, 192 (06) : 683 - 694
  • [10] Synthesis of Fluorinated Cyclopropyl Amino Acid Analogues: Toward the Synthesis of Original Fluorinated Peptidomimetics.
    Milanole, Gaelle
    Couve-Bonnaire, Samuel
    Bonfanti, Jean-Francois
    Jubault, Philippe
    Pannecoucke, Xavier
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (02): : 212 - 223
12345