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The total synthesis of 1\u2010hydroxyboivinianin A and its enantiomer was completed in a six\u2010step sequence in 42\u2009% overall yield. The synthesis leveraged a key diastereoselective nucleophilic addition with chiral imidazolidinone to establish the benzylic tertiary alcohol and intramolecular Horner\u2010Wadsworth Emmons to furnish the lactone. Both enantiomers were found to have negligible antibacterial activity against a panel of gram\u2010positive and negative bacteria and minimal antifungal activity against phytopathogens. Investigations of a possible <jats:italic>in\u2005vitro<\/jats:italic> lactone hydrolysis to produce an inactive linear acid led to the discovery of a spontaneous cyclization, suggesting the lactone is resistant to hydrolysis and the lactone is not degrading to produce an inactive species.<\/jats:p>","DOI":"10.1002\/cmdc.202200363","type":"journal-article","created":{"date-parts":[[2022,9,21]],"date-time":"2022-09-21T09:44:29Z","timestamp":1663753469000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Total Synthesis and Antibacterial Investigations of 1\u2010Hydroxyboivinianin A"],"prefix":"10.1002","volume":"17","author":[{"given":"Ingrid K.","family":"Wilt","sequence":"first","affiliation":[{"name":"Department of Chemistry Emory University  1515 Dickey Drive Atlanta GA 30322 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Adrian R.","family":"Demeritte","sequence":"additional","affiliation":[{"name":"Department of Chemistry Emory University  1515 Dickey Drive Atlanta GA 30322 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Weiwei","family":"Wang","sequence":"additional","affiliation":[{"name":"Corteva Agriscience<sup>TM<\/sup>  9330 Zionsville Road Indianapolis IN 46268 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5198-7744","authenticated-orcid":false,"given":"William M.","family":"Wuest","sequence":"additional","affiliation":[{"name":"Department of Chemistry Emory University  1515 Dickey Drive Atlanta GA 30322 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2022,10,19]]},"reference":[{"key":"e_1_2_7_1_1","doi-asserted-by":"publisher","DOI":"10.1128\/jb.52.3.393-397.1946"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1086\/491709"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.3390\/antibiotics10070842"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature14098"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1039\/b808743a"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41570-021-00313-1"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.5b00004"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules21081084"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.fitote.2018.02.031"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41429-018-0025-3"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phytol.2016.10.015"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41598-021-94823-z"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1038\/ismej.2007.92"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1038\/ismej.2012.58"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1007\/s42995-020-00037-z"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejar.2013.10.006"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1186\/s12879-020-4789-2"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.marenvres.2019.104850"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1980.1223"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2008.02.094"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1039\/p19960002129"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2021.132253"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.51.1869"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b02144"},{"key":"e_1_2_7_25_1","unstructured":"P.Gibbons K. 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