Peroxyarachidonic acid

This remarkably selective internal epoxidation of peroxyarachidonic acid to form 14,15-oxido-arachidonic acid occurs as shown because of unusually favorable stereoelectronics. The corresponding reaction sequence with eicosa-(E)-8,ll,14-trienoic acid affords the Ai4,i5 epoxide in 94% isolated yield and >95% purity. 

Corey has described routes leading to the selective epoxidation of arachidonic acid. He showed that peroxyarachidonic acid undergoes intramolecular reaction to give cw-14,15-epoxy 20 3 possibly via the cyclic intermediate shown ... 

An ingenious selective epoxidation of arachidonic acid (12) has been devised by preparing peroxyarachidonic acid (13), which internally epoxidases the 14,15-double bond, as shown in Scheme 12. The 5,6-epoxide of arachidonic acid is also available by the route shown in Scheme 13. 

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