{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,11]],"date-time":"2026-09-11T22:50:39Z","timestamp":1789167039580,"version":"build-2803163510"},"reference-count":24,"publisher":"International Union of Crystallography (IUCr)","issue":"8","license":[{"start":{"date-parts":[[2024,7,15]],"date-time":"2024-07-15T00:00:00Z","timestamp":1721001600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2024,7,15]],"date-time":"2024-07-15T00:00:00Z","timestamp":1721001600000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"DOI":"10.13039\/501100000268","name":"Biotechnology and Biological Sciences Research Council","doi-asserted-by":"publisher","award":["2110646"],"award-info":[{"award-number":["2110646"]}],"id":[{"id":"10.13039\/501100000268","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000268","name":"Biotechnology and Biological Sciences Research Council","doi-asserted-by":"publisher","award":["BB\/S00047X\/1"],"award-info":[{"award-number":["BB\/S00047X\/1"]}],"id":[{"id":"10.13039\/501100000268","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr E Cryst Commun","Acta Cryst E","Acta Cryst Sect E","Acta Crystallogr E","Acta Crystallogr Sect E","Acta Cryst E Cryst Commun","Acta Cryst Sect E Cryst Commun"],"accepted":{"date-parts":[[2024,7,2]]},"published-print":{"date-parts":[[2024,8,1]]},"abstract":"<jats:p>The X-ray crystal structure data of 12-\u03b1-fluoro-3\u03b2-hydroxyolean-28,13\u03b2-olide methanol hemisolvate, 2C<jats:sub>30<\/jats:sub>H<jats:sub>47<\/jats:sub>FO<jats:sub>3<\/jats:sub>\u00b7CH<jats:sub>3<\/jats:sub>OH, (<jats:bold>1<\/jats:bold>), and 12-\u03b1-fluoro-3\u03b2-hydroxytaraxer-28,14\u03b2-olide methanol hemisolvate, 2C<jats:sub>30<\/jats:sub>H<jats:sub>47<\/jats:sub>FO<jats:sub>3<\/jats:sub>\u00b7CH<jats:sub>3<\/jats:sub>OH, (<jats:bold>2<\/jats:bold>), are described. The fluorolactonization of oleanolic acid using Selectfluor<jats:sup>TM<\/jats:sup> yielded a mixture of the six-membered \u03b4-lactone (<jats:bold>1<\/jats:bold>) and the unusual seven-membered \u03b3-lactone (<jats:bold>2<\/jats:bold>) following a 1,2-shift of methyl C-27 from C-14 to C-13.<\/jats:p>","DOI":"10.1107\/s2056989024006480","type":"journal-article","created":{"date-parts":[[2024,7,16]],"date-time":"2024-07-16T08:41:47Z","timestamp":1721119307000},"page":"857-862","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":1,"title":["Structural determination of oleanane-28,13\u03b2-olide and taraxerane-28,14\u03b2-olide fluorolactonization products from the reaction of oleanolic acid with Selectfluor<sup>TM<\/sup>"],"prefix":"10.1107","volume":"80","author":[{"given":"Megan A.","family":"Eadsforth","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Linghan","family":"Kong","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1949-4250","authenticated-orcid":true,"given":"George","family":"Whitehead","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"I\u00f1igo J.","family":"Vit\u00f3rica-Yrez\u00e1bal","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Raymond T.","family":"O'Keefe","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Richard A.","family":"Bryce","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Roger C.","family":"Whitehead","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2024,7,15]]},"reference":[{"key":"yy2009_bb1","doi-asserted-by":"crossref","unstructured":"Adjei, S., Amponsah, I. K., Bekoe, S. O., Harley, B. K., Mensah, K. B., Mensah, A. Y., Baah, M. K. & Fosu-Mensah, G. (2021). Heliyon, 7, e07910. https:\/doi.org\/10.1016\/j.heliyon.2021.e07910","DOI":"10.1016\/j.heliyon.2021.e07910"},{"key":"yy2009_bb2","doi-asserted-by":"crossref","first-page":"4957","DOI":"10.3390\/molecules26164957","volume":"26","author":"Baer-Dubowska","year":"2021","journal-title":"Molecules"},{"key":"yy2009_bb3","doi-asserted-by":"crossref","first-page":"4097","DOI":"10.3390\/molecules24224097","volume":"24","author":"Borella","year":"2019","journal-title":"Molecules"},{"key":"yy2009_bb4","doi-asserted-by":"crossref","first-page":"1160","DOI":"10.1021\/np50110a005","volume":"57","author":"Cheriti","year":"1994","journal-title":"J. Nat. Prod."},{"key":"yy2009_bb5","doi-asserted-by":"crossref","first-page":"1354","DOI":"10.1021\/ja00839a011","volume":"97","author":"Cremer","year":"1975","journal-title":"J. Am. Chem. Soc."},{"key":"yy2009_bb6","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1107\/S0021889808042726","volume":"42","author":"Dolomanov","year":"2009","journal-title":"J. Appl. Cryst."},{"key":"yy2009_bb8","unstructured":"Eadsforth, M. A. (2022). Expanding the toolbox for studying the splicing mechanism: Development of semi-synthetic triterpene derivatives as novel small molecule inhibitors of pre-mRNA splicing. Thesis, University of Manchester, UK."},{"key":"yy2009_bb9","doi-asserted-by":"crossref","first-page":"o679","DOI":"10.1107\/S160053681100585X","volume":"67","author":"Froelich","year":"2011","journal-title":"Acta Cryst. E"},{"key":"yy2009_bb10","doi-asserted-by":"crossref","first-page":"108853","DOI":"10.1016\/j.steroids.2021.108853","volume":"172","author":"Heise","year":"2021","journal-title":"Steroids"},{"key":"yy2009_bb11","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/j.fitote.2011.09.009","volume":"83","author":"Hu","year":"2012","journal-title":"Fitoterapia"},{"key":"yy2009_bb12","doi-asserted-by":"crossref","first-page":"1606","DOI":"10.1021\/np068014r","volume":"69","author":"Kuroda","year":"2006","journal-title":"J. Nat. Prod."},{"key":"yy2009_bb13","doi-asserted-by":"crossref","first-page":"1635","DOI":"10.1002\/cmdc.201200282","volume":"7","author":"Leal","year":"2012","journal-title":"ChemMedChem"},{"key":"yy2009_bb14","doi-asserted-by":"crossref","first-page":"792","DOI":"10.1016\/j.tet.2014.12.064","volume":"71","author":"Martinez","year":"2015","journal-title":"Tetrahedron"},{"key":"yy2009_bb15","doi-asserted-by":"crossref","first-page":"249","DOI":"10.1107\/S2052519213010014","volume":"69","author":"Parsons","year":"2013","journal-title":"Acta Cryst. B"},{"key":"yy2009_bb16","doi-asserted-by":"crossref","first-page":"20","DOI":"10.1080\/10286020903405456","volume":"12","author":"Qian","year":"2010","journal-title":"J. Asian Nat. Prod. Res."},{"key":"yy2009_bb17","unstructured":"Rigaku OD (2020). CrysAlis PRO. Rigaku Corporation, Wroclaw, Poland."},{"key":"yy2009_bb18","doi-asserted-by":"crossref","first-page":"508","DOI":"10.1039\/B814448F","volume":"7","author":"Salvador","year":"2009","journal-title":"Org. Biomol. Chem."},{"key":"yy2009_bb19","doi-asserted-by":"crossref","first-page":"12173","DOI":"10.1021\/jf403154e","volume":"61","author":"S\u00e1nchez-Quesada","year":"2013","journal-title":"J. Agric. Food Chem."},{"key":"yy2009_bb20","doi-asserted-by":"crossref","first-page":"o2139","DOI":"10.1107\/S160053681002903X","volume":"66","author":"Santos","year":"2010","journal-title":"Acta Cryst. E"},{"key":"yy2009_bb21","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","volume":"64","author":"Sheldrick","year":"2008","journal-title":"Acta Cryst. A"},{"key":"yy2009_bb22","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053273314026370","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. A"},{"key":"yy2009_bb23","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"},{"key":"yy2009_bb25","doi-asserted-by":"crossref","first-page":"10862","DOI":"10.1039\/C3RA46492J","volume":"4","author":"Tang","year":"2014","journal-title":"RSC Adv."},{"key":"yy2009_bb26","doi-asserted-by":"crossref","first-page":"706","DOI":"10.1016\/j.ejmech.2018.12.046","volume":"164","author":"Zhong","year":"2019","journal-title":"Eur. J. Med. Chem."}],"container-title":["Acta Crystallographica Section E Crystallographic Communications"],"original-title":[],"link":[{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2024\/08\/00\/yy2009\/yy2009.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2024\/08\/00\/yy2009\/yy2009.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,9,3]],"date-time":"2024-09-03T14:59:29Z","timestamp":1725375569000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S2056989024006480"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,7,15]]},"references-count":24,"journal-issue":{"issue":"8","published-online":{"date-parts":[[2024,8]]}},"alternative-id":["S2056989024006480"],"URL":"https:\/\/doi.org\/10.1107\/s2056989024006480","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S2056989024006480\/yy2009sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989024006480\/yy20091sup2.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989024006480\/yy20091sup4.mol","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989024006480\/yy20092sup3.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989024006480\/yy20092sup5.mol","asserted-by":"subject"}]},"ISSN":["2056-9890"],"issn-type":[{"value":"2056-9890","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,7,15]]},"assertion":[{"value":"Acta Crystallographica Section E: Crystallographic Communications","order":0,"name":"journal","label":"Publication","explanation":{"URL":"https:\/\/journals.iucr.org\/e"},"group":{"name":"general","label":"General"}},{"value":"research communications","order":1,"name":"content_type","label":"Content type","explanation":{"URL":"https:\/\/journals.iucr.org\/e\/services\/notesforauthors.html"},"group":{"name":"general","label":"General"}},{"value":"Available","URL":"https:\/\/scripts.iucr.org\/cgi-bin\/citedin?yy2009","order":2,"name":"article_metrics","label":"Article metrics","group":{"name":"general","label":"General"}},{"value":"Yes","order":0,"name":"peer_reviewed","label":"Peer reviewed","group":{"name":"peer_review","label":"Peer review"}},{"value":"Single blind","order":1,"name":"review_process","label":"Review process","group":{"name":"peer_review","label":"Peer review"}},{"value":"12 January 2024","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"2 July 2024","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"15 July 2024","order":2,"name":"published_online","label":"Published online","group":{"name":"publication_history","label":"Publication history"}},{"value":"This article has supporting information","name":"supplementary_materials","label":"Supplementary materials","explanation":{"URL":"https:\/\/scripts.iucr.org\/cgi-bin\/sendsup?yy2009"}},{"value":"\u00a9 2024 Eadsforth et al.","order":0,"name":"copyright","label":"Copyright","explanation":{"URL":"https:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},"group":{"name":"copyright_and_licencing","label":"Copyright and licencing"}},{"value":"Creative Commons Attribution (CC-BY)","order":1,"name":"license","label":"Licence","explanation":{"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},"group":{"name":"copyright_and_licencing","label":"Copyright and licencing"}}]}}