Bicyclo(3.2.1)octane neolignans are a biologically important class of neolignan-type compounds which are further subdivided in 7.1',8.3'-connected (or guianin-type) and 7.3',8.5'-connected (or macrophyllin-type) [1]. Although the guianin-type is the most known bicyclooctanoids, the macrophyllin-type has shown a relevant PAF-antagonistic activity [2]. A set of thirteen bicyclooctanoids (twelve of the macrophyllin-type) were isolated from the leaves of three Lauraceae species (P. cinereum, O. macrophylla and N. amazonum). Ten of them were found to have novel structures which were fully determined by spectroscopic methods as well as the absolute configuration by chirooptical methods. All bicyclooctanoids showed a significant inhibitory activity in the PAF-induced aggregation of rabbit platelets assay [3]. The new bicyclo(3.2.1)octane neolignan named as cinerin B (IC50 1.5µM) was found to be one of the most potent PAF-antagonist. For this reason, a valuable route toward its total synthesis was accomplished through dihydrobenzofuran intermediate which was obtained via a new, efficient Pd-catalysed oxyarylation reaction, starting from resorcinol and 5-methoxy-piperonal, affording the desired product in seven steps.