Abstract The intermolecular meta photocycloaddition of 1, 3-dihydroisobenzofuran and 1, 3- dihydroisoindole-2-carboxylic acid methyl ester with cyclopentene and 2, 5-dihydrofuran affords two new classes of photoadducts. The photoadducts were identified by the SORT&gen algorithm as New Molecular Entities in two-dimensional scaffold space. The structures of the adducts were established by NMR spectroscopy and the stereo-, regio- ...