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Its synthetic value arises from the efficient transfer of stereochemical information through a highly ordered six-membered transition state, enabling rapid increases in molecular complexity under mild reaction conditions. This review highlights recent applications of the Ireland\u2013Claisen rearrangement in natural product total synthesis, covering literature published during 2015\u20132025. The examples discussed demonstrate the broad utility of this transformation across structurally diverse natural product classes and illustrate how substrate structure, enolization conditions, and reaction design determine the stereochemical outcome in complex synthetic settings.<\/jats:p>","DOI":"10.1021\/acsomega.6c05600","type":"journal-article","created":{"date-parts":[[2026,7,10]],"date-time":"2026-07-10T23:38:02Z","timestamp":1783726682000},"page":"43036-43051","source":"Crossref","is-referenced-by-count":3,"title":["Ireland\u2013Claisen\nRearrangement as a Stereocontrolled\nBond-Construction Strategy in Natural Product Total Synthesis"],"prefix":"10.1021","volume":"11","author":[{"given":"Guna","family":"Sakaine","sequence":"first","affiliation":[{"name":"Latvian Institute of Organic Synthesis , , Aizkraukles 21 , ,","place":["Riga, Latvia, 1006"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nikla\u0305vs","family":"U\u0305dris","sequence":"additional","affiliation":[{"name":"Latvian Institute of Organic Synthesis , , Aizkraukles 21 , ,","place":["Riga, Latvia, 1006"]},{"name":"Riga Technical University , , Paula Valdena 3 , ,","place":["Riga, Latvia, LV-1048"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5044-4169","authenticated-orcid":true,"given":"Gints","family":"S\u030cmits","sequence":"additional","affiliation":[{"name":"Latvian Institute of Organic Synthesis , , Aizkraukles 21 , ,","place":["Riga, Latvia, 1006"]},{"name":"Riga Technical University , , Paula Valdena 3 , ,","place":["Riga, Latvia, LV-1048"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,7,10]]},"reference":[{"issue":"16","key":"2026072810092592400_cit1","doi-asserted-by":"publisher","first-page":"5897","DOI":"10.1021\/ja00771a062","article-title":"Claisen rearrangement of allyl esters","volume":"94","author":"Ireland","year":"1972","journal-title":"J. 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Soc."},{"issue":"2","key":"2026072810092592400_cit5","doi-asserted-by":"publisher","first-page":"650","DOI":"10.1021\/jo00002a030","article-title":"Stereochemical\ncontrol in the ester enolate Claisen rearrangement. 1. Stereoselectivity\nin silyl ketene acetal formation","volume":"56","author":"Ireland","year":"1991","journal-title":"J. Org. Chem."},{"issue":"11","key":"2026072810092592400_cit6","doi-asserted-by":"publisher","first-page":"3572","DOI":"10.1021\/jo00011a023","article-title":"Stereochemical control in the ester\nenolate Claisen rearrangement. 2. Chairlike vs boatlike transition-state\nselection","volume":"56","author":"Ireland","year":"1991","journal-title":"J. Org. Chem."},{"issue":"1","key":"2026072810092592400_cit7","doi-asserted-by":"publisher","first-page":"43","DOI":"10.1039\/a706415b","article-title":"Asymmetric Claisen\nrearrangement","volume":"28","author":"Ito","year":"1999","journal-title":"Chem. Soc. 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