{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,16]],"date-time":"2026-10-16T13:45:15Z","timestamp":1792158315076,"version":"4.4.0"},"reference-count":33,"publisher":"American Chemical Society (ACS)","issue":"41","license":[{"start":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T00:00:00Z","timestamp":1791244800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T00:00:00Z","timestamp":1791244800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T00:00:00Z","timestamp":1791244800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100003704","name":"Korea Research Institute of Chemical Technology","doi-asserted-by":"publisher","award":["DK2683-01"],"award-info":[{"award-number":["DK2683-01"]}],"id":[{"id":"10.13039\/501100003704","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003704","name":"Korea Research Institute of Chemical Technology","doi-asserted-by":"publisher","award":["KK2531-10"],"award-info":[{"award-number":["KK2531-10"]}],"id":[{"id":"10.13039\/501100003704","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100014188","name":"Ministry of Science and ICT, South Korea","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100014188","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003725","name":"National Research Foundation of Korea","doi-asserted-by":"publisher","award":["NRF-RS-2023-00235550"],"award-info":[{"award-number":["NRF-RS-2023-00235550"]}],"id":[{"id":"10.13039\/501100003725","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,10,16]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>We report the development of synthetic routes to representative Bauhinia family natural products, including pacharin, bauhiniastatins 1\u20134, and bauhinoxepins C\u2013J. The key transformation involves a one-pot aldol condensation\/SNAr sequence to efficiently construct the dibenzo[b,f]oxepine core. Subsequently, a cyano group, employed as a reactive handle in the aldol reaction, was removed via decyanation. Through diverse functional group transformations, a total of 28 Bauhinia family analogs were successfully synthesized, including the originally misassigned bauhinoxepin F (3d). In addition, the structure of bauhinoxepin F was subsequently revised based on our synthetic studies.<\/jats:p>","DOI":"10.1021\/acs.joc.6c01760","type":"journal-article","created":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T16:01:46Z","timestamp":1791302506000},"page":"13710-13723","source":"Crossref","is-referenced-by-count":0,"title":["A Modular and Divergent\nStrategy for Dibenzo[\n                    <i>b,f<\/i>\n                    ]oxepine Natural Products:\nTotal Syntheses of Pacharin,\nBauhiniastatins 1\u20134, and Bauhinoxepins C\u2013J and Structural\nRevision of Bauhinoxepin F"],"prefix":"10.1021","volume":"91","author":[{"given":"Sun-Gil","family":"Park","sequence":"first","affiliation":[{"name":"Korea Research Institute of Chemical Technology , , ,","place":["Daejeon, Republic of Korea, 34114"]},{"name":"Chungnam National University , , ,","place":["Daejeon, Republic of Korea, 34134"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yina","family":"Kim","sequence":"additional","affiliation":[{"name":"Korea Research Institute of Chemical Technology , , ,","place":["Daejeon, Republic of Korea, 34114"]},{"name":"Chungnam National University , , ,","place":["Daejeon, Republic of Korea, 34134"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hye Seung","family":"Ko","sequence":"additional","affiliation":[{"name":"Korea Research Institute of Chemical Technology , , ,","place":["Daejeon, Republic of Korea, 34114"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1226-6335","authenticated-orcid":true,"given":"Jung-Nyoung","family":"Heo","sequence":"additional","affiliation":[{"name":"Korea Research Institute of Chemical Technology , , ,","place":["Daejeon, Republic of Korea, 34114"]},{"name":"Chungnam National University , , ,","place":["Daejeon, Republic of Korea, 34134"]},{"name":"Korea Research Institute of Chemical Technology , , ,","place":["Daejeon, Republic of Korea, 34114"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,10,6]]},"reference":[{"key":"2026101608072317600_cit1a","doi-asserted-by":"publisher","first-page":"4245","DOI":"10.1016\/S0040-4020(01)98799-X","article-title":"Pacharin: A New\nDibenzo[2,3-6,7]oxepin Derivative from Bauhinia racemosa Lamk","volume":"40","author":"Anjaneyulu","year":"1984","journal-title":"Tetrahedron"},{"key":"2026101608072317600_cit1b","doi-asserted-by":"publisher","first-page":"879","DOI":"10.1016\/S0031-9422(03)00416-3","article-title":"A Flavanone\nand a Dihydrodibenzoxepin from Bauhinia variegata","volume":"64","author":"Reddy","year":"2003","journal-title":"Phytochemisty"},{"key":"2026101608072317600_cit1c","doi-asserted-by":"publisher","first-page":"323","DOI":"10.1021\/np058075+","article-title":"Antineoplastic Agents.\n551. Isolation and Structures of Bauhiniastatins 1\u20134 from Bauhinia purpurea","volume":"69","author":"Pettit","year":"2006","journal-title":"J. Nat. Prod."},{"key":"2026101608072317600_cit1d","doi-asserted-by":"publisher","first-page":"649","DOI":"10.1080\/10286020600979860","article-title":"New Dibenz[b,f]oxepins from Cercis chinensis Bunge","volume":"9","author":"Mu","year":"2007","journal-title":"J. Asian Nat. Prod. Res."},{"key":"2026101608072317600_cit2a","doi-asserted-by":"publisher","first-page":"12066","DOI":"10.3390\/ijms241512066","article-title":"Dibenzo[b,f]oxepine\nMolecules Used\nin Biological Systems and Medicine","volume":"24","author":"Krawczyk","year":"2023","journal-title":"Int. J.\nMol. Sci."},{"key":"2026101608072317600_cit2b","doi-asserted-by":"publisher","DOI":"10.1002\/cbdv.202200484","article-title":"An Updated\nReview on Biologically Promising Natural Oxepines","volume":"19","author":"Mandal","year":"2022","journal-title":"Chem. Biodiversity"},{"key":"2026101608072317600_cit3a","doi-asserted-by":"publisher","first-page":"795","DOI":"10.1021\/np070010e","article-title":"Bioactive Compounds from Bauhinia purpurea Possessing Antimalarial, Antimycobacterial,\nAntifungal, Anti-inflammatory, and Cytotoxic Activities","volume":"70","author":"Boonphong","year":"2007","journal-title":"J. Nat. Prod."},{"key":"2026101608072317600_cit3b","doi-asserted-by":"publisher","first-page":"213","DOI":"10.1002\/bkcs.12656","article-title":"Synthesis\nand biological evaluation of benzoxepinoindol-1-one analogs as Brd4\nbromodomain inhibitors","volume":"44","author":"Jung","year":"2023","journal-title":"Bull. Korean Chem. 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J."},{"key":"2026101608072317600_cit14b","doi-asserted-by":"publisher","first-page":"2701","DOI":"10.1021\/ol016285h","article-title":"Studies toward\nthe Total Synthesis of Popolohuanone E: Enantioselective Synthesis\nof 8-O-Methylpopolohuanone","volume":"3","author":"Katoh","year":"2001","journal-title":"Org. Lett."},{"key":"2026101608072317600_cit15","doi-asserted-by":"publisher","first-page":"511","DOI":"10.3987\/COM-21-S(R)1","article-title":"Lipase-Catalyzed\nSite-Selective Deacetylation\nof 2-Methoxy-3-methylnaphthalene-1,4-diol diacetate for Construction\nof Characteristic Substituted 1,2,3,4-Tetrahydroisoquinoline Derivative\nof Novel Ecteinascidin Marine Natural Product","volume":"105","author":"Yokoya","year":"2022","journal-title":"Heterocycles"}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.joc.6c01760","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/91\/41\/13710\/68762042\/acs.joc.6c01760.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/91\/41\/13710\/68762042\/acs.joc.6c01760.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,16]],"date-time":"2026-10-16T12:50:04Z","timestamp":1792155004000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/joceah\/article\/91\/41\/13710\/5445540\/A-Modular-and-Divergent-Strategy-for-Dibenzo-b-f"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,10,6]]},"references-count":33,"journal-issue":{"issue":"41","published-online":{"date-parts":[[2026,10,6]]},"published-print":{"date-parts":[[2026,10,16]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.joc.6c01760","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,10,6]]}}}