{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,2]],"date-time":"2026-07-02T19:01:57Z","timestamp":1783018917419,"version":"3.54.6"},"reference-count":55,"publisher":"Royal Society of Chemistry (RSC)","issue":"47","license":[{"start":{"date-parts":[[2025,11,12]],"date-time":"2025-11-12T00:00:00Z","timestamp":1762905600000},"content-version":"vor","delay-in-days":315,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/3.0\/"}],"funder":[{"DOI":"10.13039\/100000002","name":"National Institutes of Health","doi-asserted-by":"publisher","award":["AI150466"],"award-info":[{"award-number":["AI150466"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000002","name":"National Institutes of Health","doi-asserted-by":"publisher","award":["P30CA023168"],"award-info":[{"award-number":["P30CA023168"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["rsc.org"],"crossmark-restriction":true},"short-container-title":["Org. Biomol. Chem."],"abstract":"<jats:p>Substrates containing a \u03b2-chiral center provided good yields and high diastereoselectivity for cycloadducts forming 5- and 6-membered rings.<\/jats:p>","DOI":"10.1039\/d5ob01429h","type":"journal-article","created":{"date-parts":[[2025,11,12]],"date-time":"2025-11-12T15:27:42Z","timestamp":1762961262000},"page":"10701-10723","update-policy":"https:\/\/doi.org\/10.1039\/rsc_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Diastereoselective intramolecular oxidopyrylium\u2013alkene [5 + 2]-cycloaddition of substrates with a \u03b2-chiral center on alkene tethers: synthesis of 8-oxabicyclo-[3.2.1]-octenone heterocycles"],"prefix":"10.1039","volume":"23","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2472-1841","authenticated-orcid":false,"given":"Arun K.","family":"Ghosh","sequence":"first","affiliation":[{"name":"Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907, USA"},{"name":"Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, 560 Oval Drive, West Lafayette, IN 47907, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Denver","family":"Hopkins","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"292","published-online":{"date-parts":[[2025]]},"reference":[{"key":"D5OB01429H\/cit1\/1","doi-asserted-by":"crossref","first-page":"2501","DOI":"10.1016\/j.tet.2018.04.006","volume":"74","author":"Bejcek","year":"2018","journal-title":"Tetrahedron"},{"key":"D5OB01429H\/cit2\/1","doi-asserted-by":"crossref","first-page":"3405","DOI":"10.1016\/j.tet.2008.01.049","volume":"64","author":"Singh","year":"2008","journal-title":"Tetrahedron"},{"key":"D5OB01429H\/cit3\/1","doi-asserted-by":"crossref","first-page":"1859","DOI":"10.1039\/C8CC09077G","volume":"55","author":"Gao","year":"2019","journal-title":"Chem. Commun."},{"key":"D5OB01429H\/cit4\/1","doi-asserted-by":"crossref","first-page":"2244","DOI":"10.1021\/cr300087g","volume":"113","author":"Ylijoki","year":"2013","journal-title":"Chem. Rev."},{"key":"D5OB01429H\/cit5\/1","doi-asserted-by":"crossref","first-page":"1551","DOI":"10.1002\/adsc.201701379","volume":"360","author":"Pellissier","year":"2018","journal-title":"Adv. Synth. Catal."},{"key":"D5OB01429H\/cit6\/1","doi-asserted-by":"crossref","first-page":"1217","DOI":"10.1039\/C7QO01123G","volume":"5","author":"Liu","year":"2018","journal-title":"Org. Chem. Front."},{"key":"D5OB01429H\/cit7\/1","doi-asserted-by":"crossref","first-page":"3583","DOI":"10.1016\/S0968-0896(02)00244-4","volume":"10","author":"Meltzer","year":"2002","journal-title":"Bioorg. Med. Chem."},{"key":"D5OB01429H\/cit8\/1","doi-asserted-by":"crossref","first-page":"2661","DOI":"10.1021\/jm9703045","volume":"40","author":"Meltzer","year":"1997","journal-title":"J. Med. Chem."},{"key":"D5OB01429H\/cit9\/1","doi-asserted-by":"crossref","first-page":"1832","DOI":"10.1016\/j.bmc.2007.11.009","volume":"16","author":"Meltzer","year":"2008","journal-title":"Bioorg. Med. Chem."},{"key":"D5OB01429H\/cit10\/1","first-page":"71","volume":"13","author":"Radhakrishnan","year":"2008","journal-title":"Top. Curr. Chem."},{"key":"D5OB01429H\/cit11\/1","doi-asserted-by":"crossref","first-page":"7897","DOI":"10.1021\/ja9706256","volume":"119","author":"Wender","year":"1997","journal-title":"J. Am. Chem. Soc."},{"key":"D5OB01429H\/cit12\/1","doi-asserted-by":"crossref","first-page":"12976","DOI":"10.1021\/ja972279y","volume":"119","author":"Wender","year":"1997","journal-title":"J. Am. Chem. Soc."},{"key":"D5OB01429H\/cit13\/1","volume-title":"Naturally Occurring Phorbol Esters","year":"1986","unstructured":"Naturally Occurring Phorbol Esters , ed.  F. J. Evans ,  CRC Press ,  Boca Raton, FL ,  1986"},{"key":"D5OB01429H\/cit14\/1","doi-asserted-by":"crossref","first-page":"9780","DOI":"10.1021\/jo035259p","volume":"68","author":"L\u00f3pez","year":"2003","journal-title":"J. Org. Chem."},{"key":"D5OB01429H\/cit15\/1","doi-asserted-by":"crossref","first-page":"884","DOI":"10.1002\/1521-3765(20020215)8:4<884::AID-CHEM884>3.0.CO;2-Q","volume":"8","author":"L\u00f3pez","year":"2002","journal-title":"Chem. \u2013Eur. J."},{"key":"D5OB01429H\/cit16\/1","doi-asserted-by":"crossref","first-page":"4829","DOI":"10.1016\/j.tet.2004.04.003","volume":"60","author":"Krishna","year":"2004","journal-title":"Tetrahedron"},{"key":"D5OB01429H\/cit17\/1","doi-asserted-by":"crossref","first-page":"8219","DOI":"10.1021\/ja102927n","volume":"132","author":"Nicolaou","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"D5OB01429H\/cit18\/1","doi-asserted-by":"crossref","first-page":"5901","DOI":"10.1021\/ol062581o","volume":"8","author":"Roethle","year":"2006","journal-title":"Org. Lett."},{"key":"D5OB01429H\/cit19\/1","doi-asserted-by":"crossref","first-page":"703","DOI":"10.1021\/acs.accounts.9b00640","volume":"53","author":"Min","year":"2020","journal-title":"Acc. Chem. Res."},{"key":"D5OB01429H\/cit20\/1","doi-asserted-by":"crossref","first-page":"5912","DOI":"10.1002\/anie.201402834","volume":"53","author":"Witten","year":"2014","journal-title":"Angew. Chem., Int. Ed."},{"key":"D5OB01429H\/cit21\/1","doi-asserted-by":"crossref","first-page":"14578","DOI":"10.1021\/ja206997e","volume":"133","author":"Burns","year":"2011","journal-title":"J. Am. Chem. Soc."},{"key":"D5OB01429H\/cit22\/1","doi-asserted-by":"crossref","first-page":"4215","DOI":"10.1039\/c2ob07007c","volume":"10","author":"Tchabanenko","year":"2012","journal-title":"Org. Biomol. Chem."},{"key":"D5OB01429H\/cit23\/1","doi-asserted-by":"crossref","first-page":"152377","DOI":"10.1016\/j.tetlet.2020.152377","volume":"61","author":"Rokey","year":"2020","journal-title":"Tetrahedron Lett."},{"key":"D5OB01429H\/cit24\/1","doi-asserted-by":"crossref","first-page":"8127","DOI":"10.1021\/acs.joc.1c00600","volume":"86","author":"Ghosh","year":"2021","journal-title":"J. Org. Chem."},{"key":"D5OB01429H\/cit25\/1","first-page":"1","volume-title":"Organic Reactions","volume":"19","year":"1972","unstructured":"Organic Reactions , ed.  W.\nG. Dauben ,  Wiley ,  1972 , vol.  19 , pp.  1\u2013114"},{"key":"D5OB01429H\/cit26\/1","doi-asserted-by":"crossref","first-page":"1630","DOI":"10.1021\/jo50012a009","volume":"17","author":"Gilman","year":"1952","journal-title":"J. Org. Chem."},{"key":"D5OB01429H\/cit27\/1","doi-asserted-by":"crossref","first-page":"1295","DOI":"10.1016\/S0040-4039(00)78044-0","volume":"17","author":"Hosomi","year":"1976","journal-title":"Tetrahedron Lett."},{"key":"D5OB01429H\/cit28\/1","doi-asserted-by":"crossref","first-page":"8646","DOI":"10.1021\/jo0105641","volume":"66","author":"Lee","year":"2001","journal-title":"J. Org. Chem."},{"key":"D5OB01429H\/cit29\/1","doi-asserted-by":"crossref","first-page":"4847","DOI":"10.1021\/acs.joc.6b00469","volume":"81","author":"Li","year":"2016","journal-title":"J. Org. Chem."},{"key":"D5OB01429H\/cit30\/1","doi-asserted-by":"crossref","first-page":"111564","DOI":"10.1039\/C6RA22611F","volume":"6","author":"Ghosh","year":"2016","journal-title":"RSC Adv."},{"key":"D5OB01429H\/cit31\/1","doi-asserted-by":"crossref","first-page":"e202116136","DOI":"10.1002\/anie.202116136","volume":"61","author":"Ji","year":"2022","journal-title":"Angew. Chem., Int. Ed."},{"key":"D5OB01429H\/cit32\/1","doi-asserted-by":"crossref","first-page":"12331","DOI":"10.1021\/acs.joc.4c01262","volume":"89","author":"Ghosh","year":"2024","journal-title":"J. Org. Chem."},{"key":"D5OB01429H\/cit33\/1","doi-asserted-by":"crossref","first-page":"8685","DOI":"10.1016\/j.tetlet.2005.10.050","volume":"46","author":"Feng","year":"2005","journal-title":"Tetrahedron Lett."},{"key":"D5OB01429H\/cit34\/1","doi-asserted-by":"crossref","first-page":"2253","DOI":"10.1016\/0040-4039(76)80042-1","volume":"17","author":"Kuwajima","year":"1976","journal-title":"Tetrahedron Lett."},{"key":"D5OB01429H\/cit35\/1","doi-asserted-by":"crossref","first-page":"2247","DOI":"10.1039\/p19850002247","author":"Wessel","year":"1985","journal-title":"J. Chem. Soc., Perkin Trans. 1"},{"key":"D5OB01429H\/cit36\/1","doi-asserted-by":"crossref","first-page":"5187","DOI":"10.1021\/acs.joc.8b00593","volume":"83","author":"Ghosh","year":"2018","journal-title":"J. Org. Chem."},{"key":"D5OB01429H\/cit37\/1","doi-asserted-by":"crossref","first-page":"9228","DOI":"10.1021\/ja203034k","volume":"133","author":"Wender","year":"2011","journal-title":"J. Am. Chem. Soc."},{"key":"D5OB01429H\/cit38\/1","doi-asserted-by":"crossref","first-page":"1223","DOI":"10.1055\/s-2000-6409","author":"Barbero","year":"2000","journal-title":"Synthesis"},{"key":"D5OB01429H\/cit39\/1","doi-asserted-by":"crossref","first-page":"2870","DOI":"10.1021\/ja00901a059","volume":"85","author":"Karplus","year":"1963","journal-title":"J. Am. Chem. Soc."},{"key":"D5OB01429H\/cit40\/1","doi-asserted-by":"crossref","first-page":"11363","DOI":"10.1016\/S0040-4020(98)00630-9","volume":"54","author":"Constantino","year":"1998","journal-title":"Tetrahedron"},{"key":"D5OB01429H\/cit41\/1","unstructured":"Single-crystal X-ray analysis was performed in our X-ray crystallography laboratory at Purdue University, under the direction of  Dr Matthias Zeller, Department of Chemistry, Purdue University"},{"key":"D5OB01429H\/cit42\/1","doi-asserted-by":"publisher","year":"2025","unstructured":"CCDC 2411050: Experimental Crystal Structure Determination ,  2025 ,  10.5517\/ccdc.csd.cc2lxwt7","DOI":"10.5517\/ccdc.csd.cc2lxwt7"},{"key":"D5OB01429H\/cit43a\/1","doi-asserted-by":"publisher","year":"2025","unstructured":"CCDC 2470759: Experimental Crystal Structure Determination ,  2025 ,  10.5517\/ccdc.csd.cc2ny0xk","DOI":"10.5517\/ccdc.csd.cc2ny0xk"},{"key":"D5OB01429H\/cit43b\/1","doi-asserted-by":"publisher","year":"2025","unstructured":"CCDC 2408404: Experimental Crystal Structure Determination ,  2025 ,  10.5517\/ccdc.csd.cc2lv4g2","DOI":"10.5517\/ccdc.csd.cc2lv4g2"},{"key":"D5OB01429H\/cit44\/1","doi-asserted-by":"crossref","first-page":"1754","DOI":"10.1002\/anie.201410806","volume":"54","author":"Mei","year":"2015","journal-title":"Angew. Chem., Int. Ed."},{"key":"D5OB01429H\/cit45\/1","doi-asserted-by":"crossref","first-page":"9818","DOI":"10.1021\/acs.joc.8b01322","volume":"83","author":"Kaufman","year":"2018","journal-title":"J. Org. Chem."},{"key":"D5OB01429H\/cit46\/1","doi-asserted-by":"crossref","first-page":"3270","DOI":"10.1021\/ol4012986","volume":"15","author":"Woodall","year":"2013","journal-title":"Org. Lett."},{"key":"D5OB01429H\/cit47\/1","doi-asserted-by":"crossref","first-page":"6717","DOI":"10.1039\/C4OB00695J","volume":"12","author":"Kimura","year":"2014","journal-title":"Org. Biomol. Chem."},{"key":"D5OB01429H\/cit48\/1","doi-asserted-by":"crossref","first-page":"5757","DOI":"10.1021\/ja029125p","volume":"125","author":"Mart\u00edn-Matute","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"D5OB01429H\/cit49\/1","doi-asserted-by":"crossref","first-page":"487","DOI":"10.1021\/jo00002a003","volume":"56","author":"Kondo","year":"1991","journal-title":"J. Org. Chem."},{"key":"D5OB01429H\/cit50\/1","doi-asserted-by":"crossref","first-page":"1053","DOI":"10.1016\/S0040-4039(00)91857-4","volume":"33","author":"Le Roux","year":"1992","journal-title":"Tetrahedron Lett."},{"key":"D5OB01429H\/cit51\/1","doi-asserted-by":"crossref","first-page":"203","DOI":"10.1016\/S0926-860X(99)00368-3","volume":"194\u2013195","author":"Baba","year":"2000","journal-title":"Appl. Catal., A"},{"key":"D5OB01429H\/cit52\/1","doi-asserted-by":"crossref","first-page":"10789","DOI":"10.1016\/S0040-4020(99)00594-3","volume":"55","author":"Loh","year":"1999","journal-title":"Tetrahedron"},{"key":"D5OB01429H\/cit53\/1","doi-asserted-by":"crossref","first-page":"1277","DOI":"10.1007\/s12272-011-0806-8","volume":"34","author":"Park","year":"2011","journal-title":"Arch. Pharmacal Res."},{"key":"D5OB01429H\/cit54\/1","doi-asserted-by":"crossref","first-page":"14209","DOI":"10.1021\/acs.joc.4c01638","volume":"89","author":"Sutter","year":"2024","journal-title":"J. Org. Chem."}],"container-title":["Organic &amp; Biomolecular Chemistry"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/pubs.rsc.org\/en\/content\/articlepdf\/2025\/OB\/D5OB01429H","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,7,2]],"date-time":"2026-07-02T17:54:41Z","timestamp":1783014881000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.rsc.org\/ob\/article\/23\/47\/10701-10723\/903246"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025]]},"references-count":55,"journal-issue":{"issue":"47","published-print":{"date-parts":[[2025,12,3]]}},"URL":"https:\/\/doi.org\/10.1039\/d5ob01429h","relation":{},"ISSN":["1477-0520","1477-0539"],"issn-type":[{"value":"1477-0520","type":"print"},{"value":"1477-0539","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025]]}}}