Chiral Vinylphosphonate and Phosphonate Analogues of the Immunosuppressive Agent FTY720

摘要

The first enantioselective synthesis of chiral isosteric phosphonate analogues of FTY720 is described. One of these analogues, FTY720-(E)-vinylphosphonate (S)->5, but not its R enantiomer, elicited a potent anti-apoptotic effect in intestinal epithelial cells, suggesting that it exerts its action via the enantioselective activation of a receptor. (S)->5 failed to activate the sphingosine 1-phosphate type 1 (S1P1) receptor.