{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,26]],"date-time":"2026-09-26T00:36:52Z","timestamp":1790383012949,"version":"4.1.0"},"reference-count":40,"publisher":"American Chemical Society (ACS)","issue":"32","license":[{"start":{"date-parts":[[2026,8,5]],"date-time":"2026-08-05T00:00:00Z","timestamp":1785888000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,8,5]],"date-time":"2026-08-05T00:00:00Z","timestamp":1785888000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,8,5]],"date-time":"2026-08-05T00:00:00Z","timestamp":1785888000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/100016975","name":"Naohiko Fukuoka Memorial Foundation","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100016975","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001700","name":"Ministry of Education, Culture, Sports, Science and Technology","doi-asserted-by":"publisher","award":["JPMXS0440500025"],"award-info":[{"award-number":["JPMXS0440500025"]}],"id":[{"id":"10.13039\/501100001700","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100008670","name":"Terumo Foundation for Life Sciences and Arts","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100008670","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,8,14]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>A total synthesis of scytonemin and reduced scytonemin was achieved. The intramolecular Mannich reaction between the aminal group and the siloxy olefin, derived from the aldol adduct between isatin and TIPS-protected raspberry ketone, proceeded to give a tricyclic half-scytonemin skeleton. After dimerization to construct the scytonemin skeleton, oxidation with t-BuOCl provided olefins in side chains regio- and stereoselectively in high yield. Treatment of the product with DDQ afforded the scytonemin skeleton in a quantitative yield. Interconversion between protected scytonemin and protected reduced scytonemin was achieved, which could be developed as molecular machines. Additionally, the cyclic voltammetry of reduced scytonemin was disclosed.<\/jats:p>","DOI":"10.1021\/acs.joc.6c00860","type":"journal-article","created":{"date-parts":[[2026,8,5]],"date-time":"2026-08-05T20:02:09Z","timestamp":1785960129000},"page":"10850-10855","source":"Crossref","is-referenced-by-count":1,"title":["Total Synthesis of Scytonemin\nand Reduced Scytonemin"],"prefix":"10.1021","volume":"91","author":[{"given":"Yutaro","family":"Udagawa","sequence":"first","affiliation":[{"name":"Waseda University , , 3-4-1 Ohkubo , , ,","place":["Shinjuku-ku, Tokyo, Japan, 169-8555"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8036-532X","authenticated-orcid":true,"given":"Seijiro","family":"Hosokawa","sequence":"additional","affiliation":[{"name":"Waseda University , , 3-4-1 Ohkubo , , ,","place":["Shinjuku-ku, Tokyo, Japan, 169-8555"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,5]]},"reference":[{"key":"2026081410083712800_cit1a","doi-asserted-by":"publisher","first-page":"395","DOI":"10.1111\/j.0022-3646.1991.00395.x","article-title":"Characterization\nand Biological Implication of Scytonemin, A Cyanobacterial Sheath\nPigment","volume":"27","author":"Garcia-Pichel","year":"1991","journal-title":"J. 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Astrobiology"},{"key":"2026081410083712800_cit6a","doi-asserted-by":"publisher","first-page":"4458","DOI":"10.1021\/ol201812n","article-title":"Oxidative Coupling as a Biomimetic\nApproach to the Synthesis of Scytonemin","volume":"13","author":"Ekebergh","year":"2011","journal-title":"Org.\nLett."},{"key":"2026081410083712800_cit6b","doi-asserted-by":"publisher","first-page":"25630","DOI":"10.1038\/s41598-025-10419-x","article-title":"Structure\nrevison on scytonemin imine and its relationship to scytonemin chromism\nand cyanobacterial adaptability","volume":"15","author":"Larson","year":"2025","journal-title":"Sci. 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Sci."},{"key":"2026081410083712800_cit19a","doi-asserted-by":"publisher","first-page":"12847","DOI":"10.1021\/ja0743083","article-title":"Voltammetry\nof Quinones in Unbuffered Aqueous Solution:\nReassessing the Roles of Proton Transfer and Hydrogen Bonding in the\nAqueous Electrochemistry of Quinones","volume":"129","author":"Quan","year":"2007","journal-title":"J. Am.\nChem. Soc."},{"key":"2026081410083712800_cit19b","unstructured":"(b)\n          \n            \n              Jeffrey, C. S.; Barile, C. J.\n          Compositions and Methods for Making Scytonemin and Its Analogs and\nDerivatives. US 20,260,042,736 A1, 2026."},{"key":"2026081410083712800_cit20","doi-asserted-by":"publisher","first-page":"148558","DOI":"10.1016\/j.bbabio.2022.148558","article-title":"The aprotic electrochemistry of quinones","volume":"1863","author":"Prince","year":"2022","journal-title":"BBA \u2013 Bioenergetics"}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.joc.6c00860","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/91\/32\/10850\/66419085\/acs.joc.6c00860.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/91\/32\/10850\/66419085\/acs.joc.6c00860.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,14]],"date-time":"2026-08-14T14:31:26Z","timestamp":1786717886000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/joceah\/article\/91\/32\/10850\/5246532\/Total-Synthesis-of-Scytonemin-and-Reduced"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,8,5]]},"references-count":40,"journal-issue":{"issue":"32","published-online":{"date-parts":[[2026,8,5]]},"published-print":{"date-parts":[[2026,8,14]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.joc.6c00860","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,8,5]]}}}