Total synthesis of aspirin-triggered 15-epi-lipoxin A4

The total synthesis of aspirin-triggered 15-epi-LXA4 has been achieved using a chiral pool strategy for the C1–C12 fragment starting from 2-deoxy-d-ribose. Sharpless catalytic AE generated the C15 chiral center with >98% ee. The stereospecific (Z)-reduction of the conjugated trienyne to the tetraene was achieved with Zn(Cu/Ag) in aq. CH3OH at rt.