{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,27]],"date-time":"2026-05-27T20:25:56Z","timestamp":1779913556660,"version":"3.53.1"},"reference-count":47,"publisher":"Georg Thieme Verlag KG","issue":"01","funder":[{"DOI":"10.13039\/100000057","name":"National Institute of General Medical Sciences","doi-asserted-by":"crossref","award":["GM128570"],"award-info":[{"award-number":["GM128570"]}],"id":[{"id":"10.13039\/100000057","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Synthesis"],"published-print":{"date-parts":[[2024,1]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The Lycopodium alkaloid complanadine A, isolated in 2000, is a complex and unsymmetrical dimer of lycodine. Biologically, it is a novel and promising lead compound for the development of new treatments for neurodegenerative disorders and persistent pain management. Herein, we report a concise synthesis of complanadine A using a pyrrole-to-pyridine molecular editing strategy. The use of a nucleophilic pyrrole as the precursor of the desired pyridine enabled an efficient and one-pot construction of the tetracyclic core skeleton of complanadine A and lycodine. The pyrrole group was converted into a 3-chloropyridine via Ciamician\u2013Dennstedt one-carbon ring expansion. A subsequent C\u2013H arylation between the 3-chloropyridine and a pyridine N-oxide formed the unsymmetrical dimer, which was then advanced to complanadine A. Overall, from a readily available known compound, the total synthesis of complanadine A was achieved in 11 steps. The pyrrole-to-pyridine molecular editing strategy enabled us to significantly enhance the overall synthetic efficiency. Additionally, as demonstrated by Suzuki\u2013Miyaura cross-coupling, the 3-chloropyridine product from the Ciamician\u2013Dennstedt rearrangement is amenable for further derivatization, offering an opportunity for simplified analogue synthesis.<\/jats:p>","DOI":"10.1055\/a-2107-5159","type":"journal-article","created":{"date-parts":[[2023,6,7]],"date-time":"2023-06-07T23:22:57Z","timestamp":1686180177000},"page":"107-117","source":"Crossref","is-referenced-by-count":9,"title":["Concise Total Synthesis of Complanadine\u00a0A Enabled by Pyrrole-to-Pyridine Molecular Editing"],"prefix":"10.1055","volume":"56","author":[{"given":"Brandon S.","family":"Martin","sequence":"first","affiliation":[{"name":"Department of Chemistry, Purdue University"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Donghui","family":"Ma","sequence":"first","affiliation":[{"name":"Department of Chemistry, Purdue University"},{"name":"Department of Chemistry, Emory University"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7956-6426","authenticated-orcid":false,"given":"Mingji","family":"Dai","sequence":"first","affiliation":[{"name":"Department of Chemistry, Purdue University"},{"name":"Department of Chemistry, Emory University"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Takeru","family":"Saito","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Purdue University"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Katelyn S.","family":"Gallagher","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Purdue University"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"194","published-online":{"date-parts":[[2023,7,3]]},"reference":[{"key":"ref1","doi-asserted-by":"crossref","first-page":"752","DOI":"10.1039\/b409720n","volume":"21","author":"X Ma","year":"2004","journal-title":"Nat. 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