{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,18]],"date-time":"2026-09-18T14:05:41Z","timestamp":1789740341275,"version":"4.0.1"},"reference-count":24,"publisher":"American Chemical Society (ACS)","issue":"37","license":[{"start":{"date-parts":[[2027,9,8]],"date-time":"2027-09-08T00:00:00Z","timestamp":1820361600000},"content-version":"vor","delay-in-days":365,"URL":"https:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"},{"start":{"date-parts":[[2026,9,8]],"date-time":"2026-09-08T00:00:00Z","timestamp":1788825600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,9,8]],"date-time":"2026-09-08T00:00:00Z","timestamp":1788825600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,9,8]],"date-time":"2026-09-08T00:00:00Z","timestamp":1788825600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100001700","name":"Ministry of Education, Culture, Sports, Science and Technology","doi-asserted-by":"publisher","award":["23H04880"],"award-info":[{"award-number":["23H04880"]}],"id":[{"id":"10.13039\/501100001700","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001700","name":"Ministry of Education, Culture, Sports, Science and Technology","doi-asserted-by":"publisher","award":["23H04888"],"award-info":[{"award-number":["23H04888"]}],"id":[{"id":"10.13039\/501100001700","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["25K01975"],"award-info":[{"award-number":["25K01975"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002241","name":"Japan Science and Technology Agency","doi-asserted-by":"publisher","award":["JPMJSP2110"],"award-info":[{"award-number":["JPMJSP2110"]}],"id":[{"id":"10.13039\/501100002241","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,9,18]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The site-selective oxidation of C29 or C30 methyl groups in pentacyclic triterpenoids is a major synthetic challenge. Starting from betulinic acid, we developed a two-step approach involving allylic bromination followed by FeBr3\/SiO2-mediated rearrangement to provide the oleanane 28,19\u03b2-lactone skeleton with moderate C30-selectivity. The utility of the method was demonstrated by the semisynthesis of the naturally occurring triterpenoid adinandrolide (2) and C20-epi-adinandrolide (11). This method provides access to highly oxidized oleanane derivatives for biological evaluation and structure\u2013activity relationship studies.<\/jats:p>","DOI":"10.1021\/acs.joc.6c01638","type":"journal-article","created":{"date-parts":[[2026,9,8]],"date-time":"2026-09-08T17:01:53Z","timestamp":1788886913000},"page":"12768-12773","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis of C29-\nor C30-Oxidized Oleananes via Allylic\nBromination and Ring Expansion: Application to the Semisynthesis of\nAdinandrolide"],"prefix":"10.1021","volume":"91","author":[{"given":"Maki","family":"Yamanaka","sequence":"first","affiliation":[{"name":"Kyoto University , , Kitashirakawa-Oiwakecho , , ,","place":["Sakyo-ku, Kyoto, Japan, 606-8502"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9361-0857","authenticated-orcid":true,"given":"Chihiro","family":"Tsukano","sequence":"additional","affiliation":[{"name":"Kyoto University , , Kitashirakawa-Oiwakecho , , ,","place":["Sakyo-ku, Kyoto, Japan, 606-8502"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,8]]},"reference":[{"key":"2026091808082752500_cit1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biopha.2021.112397","article-title":"Anticancer activity\nof oleanolic acid and its derivatives: Recent advances in evidence,\ntarget profiling and mechanism of action","volume":"145","author":"Tang","year":"2022","journal-title":"Biomed.\nPharmacother."},{"key":"2026091808082752500_cit2","doi-asserted-by":"publisher","first-page":"1303","DOI":"10.1039\/D2NP00063F","article-title":"Natural products of\npentacyclic triterpenoids: from discovery to heterologous biosynthesis","volume":"40","author":"Li","year":"2023","journal-title":"Nat. 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