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We report the enantioselective synthesis of (+)\u2010dracocephalone A, (+)\u2010dracocequinone A, and (\u2212)\u2010dracocequinone B, featuring two strategic oxygen\u2010engaged transformations. The 2\u2010oxabicyclo[2.2.2]octane frameworks are constructed via a late\u2010stage oxygen\u2010mediated oxabridge reorganization of 6\u2010oxabicyclo[3.2.1]octane precursors. In this cascade reaction, a redox\u2010neutral disproportionation reaction generates reduced phenolic and oxidized cyclohexadienone intermediates simultaneously, followed by an oxabridge reorganization through selective C10\u2013O bond cleavage and regiospecific 1,6\u2010conjugate addition. The 6\u2010oxabicyclo[3.2.1]octane framework is formed efficiently through an oxygen\u2010engaged oxabridge cyclization. The oxabridge construction strategy demonstrated in this work will allow streamlined syntheses of oxa\u2010bridged bioactive natural products and their structural analogs.<\/jats:p>","DOI":"10.1002\/anie.3945602","type":"journal-article","created":{"date-parts":[[2026,8,29]],"date-time":"2026-08-29T12:10:40Z","timestamp":1788005440000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Enantioselective Total Synthesis of (+)\u2010Dracocephalone A, (+)\u2010Dracocequinone A, and (\u2212)\u2010Dracocequinone B by Oxabridge Construction With Oxygen"],"prefix":"10.1002","volume":"65","author":[{"given":"Kang","family":"Li","sequence":"first","affiliation":[{"name":"School of Chemistry and Chemical, Engineering University of South China  Hengyang China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yongqiang","family":"Wang","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical, 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