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Here the first enantioselective total synthesis of semi\u2010viriditoxic acid as well as the synthesis of semi\u2013viriditoxin and derivatives is reported. The key intermediate in the synthesis of naphthopyranones is an \u03b1,\u03b2\u2010unsaturated \u03b4\u2010lactone, which we synthesized in two different ways (<jats:italic>Ghosez<\/jats:italic>\u2013cyclization and <jats:italic>Grubbs<\/jats:italic> ring\u2013closing metathesis), while the domino\u2013<jats:italic>Michael<\/jats:italic>\u2013<jats:italic>Dieckmann<\/jats:italic> reaction of the \u03b1,\u03b2\u2010unsaturated \u03b4\u2010lactone with an orsellinic acid derivative is the key reaction. A structure\u2010activity relationship study was performed measuring the cytotoxicity in Burkitt B lymphoma cells (Ramos). The dimeric structure was found to be crucial for biological activity: Only the dimeric naphthopyranones showed cytotoxic and apoptotic activity, whereas the monomers did not display any activity at all.<\/jats:p>","DOI":"10.1002\/chem.202400559","type":"journal-article","created":{"date-parts":[[2024,2,27]],"date-time":"2024-02-27T10:45:27Z","timestamp":1709030727000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["From the Total Synthesis of Semi\u2013Viriditoxin, Semi\u2013Viriditoxic Acid and Dimeric Naphthopyranones to their Biological Activities in Burkitt B Cell Lymphoma"],"prefix":"10.1002","volume":"30","author":[{"given":"Frederike","family":"Weber","sequence":"first","affiliation":[{"name":"Institute for Bioorganic Chemistry Heinrich Heine University D\u00fcsseldorf in Forschungszentrum J\u00fclich  52426 J\u00fclich 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