Synthesis of chiral (alpha,alpha-difluoroalkyl)phosphonate analogues of (lyso)phosphatidic acid via hydrolytic kinetic resolution.
The hydrolytic kinetic resolution of 1,1-difluoro-3,4-epoxy-butylphosphonate using a chiral salen-Co complex was employed as a key step to obtain enantiomeric diols in 99% ee as key intermediates. The enantiomerically homogeneous (alpha,alpha-difluoroalkyl)phosphonates were obtained after selective esterification and deprotection of the corresponding phosphonates. These compounds are novel phosphatase-resistant analogues of lysophosphatidic acid and phosphatidic acid. [reaction: see text]
Xu
Yong
Y
Department of Medicinal Chemistry and Center for Cell Signaling, The University of Utah, 419 Wakara Way, Suite 205, Salt Lake City, UT 84108-1257, USA.
Prestwich
Glenn D
GD
D006868:Hydrolysis; D007700:Kinetics; D008246:Lysophospholipids / Q000138:chemical synthesis / Q000737:chemistry*; D063065:Organophosphonates; D010712:Phosphatidic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D008246:Lysophospholipids; D063065:Organophosphonates; D010712:Phosphatidic Acids