In this thesis Colm Duffy reviews the chemistry and biology of stable lipoxin analogues. Colm has prepared for the first time ever a pyridine-containing LXA4 analogue in enantiomerically pure form. Biological evaluation determined that both epimers at the benzylic position suppress key cytokines known to be involved in inflammatory disease, with the (R)-epimer proving most efficacious. Moreover the author developed an excellent route to a related thiophene-containing analogue that also showed interesting biological activity. Both routes have inspired further work in the synthesis of further heteroaromatic analogues for biological evaluation.