Total synthesis of 12(R)-HETE,12(S)-HETE,~2H_2-12(R)-HETE and LTB_4 from racemic glycidol via hydrolytic kinetic resolution

摘要

The total synthesis of 12(R)-TETE,12(S)-HETE (Samuelsson's HETE),[14,15-~2H_2]-12(R)-HETE and Leukotriene B_4 from racemic glycidol is described.The key steps are the hydrolytic kinetic resolution of racemic TES-glycidol with salen-Co catalyst and the selective oxidationof primary silyl ethers,in the presence of secondary ones,under Swern conditions to give a short entry to both enantiomers of 12-HETE and LTB_4.