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The sponge\n                    <jats:italic>Ircinia felix<\/jats:italic>\n                    was selected for the significant anti\u2010HAdV activity displayed by its organic extracts. Its chemical analysis yielded three novel sesterterpene lactams, ircinialactams J\u2212L, along with three known sesterterpene furans which structures were established by a deep spectrometric analysis. Ircinialactam J displayed significant antiviral activity against HAdV without significant cytotoxicity, showing an effectiveness 11 times greater than that of the standard treatment, cidofovir\u00ae. Comparison of the antiviral evaluation results of the isolated compounds allowed us to deduce some structure\u2010activity relationships. Mechanistic assays suggest that ircinialactam J targets an early step of the HAdV replicative cycle before HAdV genome reaches the nucleus of the host cell. The first total synthesis of ircinialactam J was also accomplished to prove the structure and to provide access to analogues. Key steps are a regio\u2010 and stereoselective construction of the trisubstituted\n                    <jats:italic>Z<\/jats:italic>\n                    \u2010olefin at \u0394\n                    <jats:sup>7<\/jats:sup>\n                    by iron\u2010catalyzed carbometallation of a homopropargylic alcohol, a stereoselective methylation to generate the stereogenic center at C18, and the formation of the (\n                    <jats:italic>Z)\u2010<\/jats:italic>\n                    \u0394\n                    <jats:sup>20<\/jats:sup>\n                    by stereoselective aldol condensation to introduce the tetronic acid unit. Ircinialactam J is a promising chemical lead to new potent antiviral drugs against HAdV infections.\n                  <\/jats:p>","DOI":"10.1002\/chem.202401844","type":"journal-article","created":{"date-parts":[[2024,9,20]],"date-time":"2024-09-20T05:53:50Z","timestamp":1726811630000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Uncovering the Potent Antiviral Activity of the Sesterterpenoids from the Sponge\n                    <i>Ircinia Felix<\/i>\n                    Against Human Adenoviruses: from the Natural Source to the Total Synthesis"],"prefix":"10.1002","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2329-2387","authenticated-orcid":false,"given":"Ana","family":"Ruiz\u2010Molina","sequence":"first","affiliation":[{"name":"Unidad Cl\u00ednica de Enfermedades Infecciosas, Microbiolog\u00eda y Parasitolog\u00eda Instituto de Biomedicina de Sevilla (IBiS) Hospital Universitario Virgen del Roc\u00edo\/CSIC\/Universidad de Sevilla  Sevilla Spain"},{"name":"Instituto de Biomedicina de Sevilla (IBiS) Hospitales Universitarios Virgen del Roc\u00edo y Virgen Macarena\/CSIC\/Universidad de Sevilla  Sevilla Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1680-4340","authenticated-orcid":false,"given":"Dawrin","family":"Pech\u2010Puch","sequence":"additional","affiliation":[{"name":"CICA-Centro Interdisciplinar de Qu\u00edmica e Biolox\u00eda Departamento de Qu\u00edmica, Facultade de Ciencias, Universidade da Coru\u00f1a  A Coru\u00f1a 15071, Spain"},{"name":"Departamento de Biolog\u00eda Marina Universidad Aut\u00f3noma de Yucat\u00e1n (UADY), Carretera M\u00e9rida-Xmatkuil  km. 15.5, A.P. 4\u2013116 Itzimn\u00e1 M\u00e9rida CP 97100 Mexico"},{"name":"Escuela Nacional de Estudios Superiores Unidad M\u00e9rida (ENES M\u00e9rida) Universidad Nacional Aut\u00f3noma de M\u00e9xico (UNAM)  Carretera M\u00e9rida-Tetiz, km 4.5 Tablaje, Catastral No. 6998, Uc\u00fa CP 97357 Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ram\u00f3n E.","family":"Mill\u00e1n","sequence":"additional","affiliation":[{"name":"CICA-Centro Interdisciplinar de Qu\u00edmica e Biolox\u00eda Departamento de Qu\u00edmica, Facultade de Ciencias, Universidade da Coru\u00f1a  A Coru\u00f1a 15071, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2422-3773","authenticated-orcid":false,"given":"Luc\u00eda","family":"Ageitos","sequence":"additional","affiliation":[{"name":"CICA-Centro Interdisciplinar de Qu\u00edmica e Biolox\u00eda Departamento de Qu\u00edmica, Facultade de Ciencias, Universidade da Coru\u00f1a  A Coru\u00f1a 15071, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3197-6132","authenticated-orcid":false,"given":"Harold","family":"Villegas\u2010Hern\u00e1ndez","sequence":"additional","affiliation":[{"name":"Departamento de Biolog\u00eda Marina Universidad Aut\u00f3noma de Yucat\u00e1n (UADY), Carretera M\u00e9rida-Xmatkuil  km. 15.5, A.P. 4\u2013116 Itzimn\u00e1 M\u00e9rida CP 97100 Mexico"},{"name":"Escuela Nacional de Estudios Superiores Unidad M\u00e9rida (ENES M\u00e9rida) Universidad Nacional Aut\u00f3noma de M\u00e9xico (UNAM)  Carretera M\u00e9rida-Tetiz, km 4.5 Tablaje, Catastral No. 6998, Uc\u00fa CP 97357 Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8166-5308","authenticated-orcid":false,"given":"Jer\u00f3nimo","family":"Pach\u00f3n","sequence":"additional","affiliation":[{"name":"Instituto de Biomedicina de Sevilla (IBiS) Hospitales Universitarios Virgen del Roc\u00edo y Virgen Macarena\/CSIC\/Universidad de Sevilla  Sevilla Spain"},{"name":"Departamento de Medicina Facultad de Medicina Universidad de Sevilla  41009 Sevilla Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7036-6217","authenticated-orcid":false,"given":"Jos\u00e9","family":"P\u00e9rez Sestelo","sequence":"additional","affiliation":[{"name":"CICA-Centro Interdisciplinar de Qu\u00edmica e Biolox\u00eda Departamento de Qu\u00edmica, Facultade de Ciencias, Universidade da Coru\u00f1a  A Coru\u00f1a 15071, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2707-1979","authenticated-orcid":false,"given":"Javier","family":"S\u00e1nchez\u2010C\u00e9spedes","sequence":"additional","affiliation":[{"name":"Unidad Cl\u00ednica de Enfermedades Infecciosas, Microbiolog\u00eda y Parasitolog\u00eda Instituto de Biomedicina de Sevilla (IBiS) Hospital Universitario Virgen del Roc\u00edo\/CSIC\/Universidad de Sevilla  Sevilla Spain"},{"name":"Instituto de Biomedicina de Sevilla (IBiS) Hospitales Universitarios Virgen del Roc\u00edo y Virgen Macarena\/CSIC\/Universidad de Sevilla  Sevilla Spain"},{"name":"CIBERINFEC, ISCIII - 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