Total synthesis of 12(R)-HETE, 12(S)-HETE, 2H2-12(R)-HETE and LTB4 from racemic glycidol via hydrolytic kinetic resolution

The total synthesis of 12(R)-HETE, 12(S)-HETE (Samuelssonʹs HETE), [14,15-2H2]-12(R)-HETE and Leukotriene B4 from racemic glycidol is described. The key steps are the hydrolytic kinetic resolution of racemic TES-glycidol with salen-Co catalyst and the selective oxidation of primary silyl ethers, in the presence of secondary ones, under Swern conditions to give a short entry to both enantiomers of 12-HETE and LTB4.