Elsevier, Tetrahedron Letters, 30(43), p. 5221-5223
DOI: 10.1016/s0040-4039(02)01058-4
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New bicyclic analogues of polyunsaturated fatty acid metabolites have been prepared using short and efficient routes. Preliminary studies of their activity as inhibitors of platelet aggregation are reported. Polyunsaturated fatty acid metabolites have key regula-tory functions in living systems and many of them have been associated with various diseases. For instance the 12(S) -hydroxy -5(Z),8(Z),10(E),14(Z)eicosatetraenoic acid (12-HETE) has been implicated in many patholo-gies including inflammation, cardiovascular problems, cancer and diabetes. 1 Since 12-HETE is relatively labile, it is important to design more stable analogues: monoaromatic derivatives, joining carbon atoms C 7 and C 11 , have been prepared previously and have shown useful biological properties as inhibitors of blood platelet aggregation. 2 Therefore, it appeared very attractive to add an extra ring joining the carbon atoms C 4 to C 7 and then giving the analogue (I) with a naphthalene core (Fig. 1).