A　series　of　tetraethyl　2,4,8,10-tetramethyl-6,12-diaryl-3,9-dioxahexacyclo[6.4.0.02,7.04,11.05,10]dodec-ane-1,5,7,11-tetracarboxylates　(simplified　as　3,9-dioxatetraasteranes)　with　C　2　-symmetric　structural　characteristics　were　synthesized　through　the　[2+2]　photocycloaddition　of　the　diethyl　2,6-dimethyl-4-aryl-4H-pyran-3,5-dicarboxylates.　Besides,　their　anti-human　immunodeficiency　virus　(HIV)-1　activities　were　evaluated　by　enzyme-linked　immunosorbent　assay　(ELISA)　assay　against　HIV-1　(IIIB)　replication　in　MT-4　cell　culture.　The　result　showed　that　the　tested　compounds　exhibited　potential　activates　with　IC　50　values　less　than　110nM.　Furthermore,　docking　study　was　carried　out　to　study　the　binding　mode　of　these　compounds.　The　results　indicated　that　the　overall　orientation　of　the　inhibitors　in　the　active　site　were　similar　to　that　of　the　cyclic　urea　AHA001　and　a　hydrogen　bond　with　the　protein　residues　might　play　a　crucial　role　in　their　anti-HIV-1　activities.　Such　results　will　provide　a　theoretical　foundation　for　further　investigations　on　the　biological　activity　of　3,9-dioxatetraasteranes.　©　2019　The　Pharmaceutical　Society　of　Japan