A general synthesis of aromatic and heteroaromatic lipoxin B analogues.

Lipoxins are an important class of pro-resolving mediators that play a crucial role in the resolution of inflammation. Thus, the synthesis of more chemically and metabolically stable synthetic lipoxin analogues is an area of significant interest. Whereas synthetic analogues of lipoxin A (LXA) have been well studied, analogues of lipoxin B (LXB) have been the focus of considerably less attention. Herein we report the asymmetric synthesis of a focused library of LXB mimetics in which the triene core of the molecule has been replaced with different aromatic and heteroaromatic rings. The synthesis of each of these analogues was achieved by a general strategy in which the key steps were a Suzuki cross coupling between a common upper chain fragment and an aromatic lower chain, followed by a stereoselective ketone reduction.