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Their acid sensitivity, together with detailed analysis of the spectroscopic data indicated that profound structural revision was necessary. This led to reassignment of aruncin B as a <jats:italic>Z<\/jats:italic>\u2010\u03b3\u2010alkylidenebutenolide <jats:italic>Z<\/jats:italic>\u2010<jats:bold>36<\/jats:bold>. Although a related RCM\/ oxyselenation\u2010selenoxide elimination sequence was used to confirm the \u03b3\u2010alkylidenebutenolide motif, a \u03b2\u2010iodo Morita\u2010Baylis\u2013Hillman reaction\/ Sonogashira cross\u2010coupling\u20105\u2010<jats:italic>exo\u2010dig<\/jats:italic> lactonisation sequence was subsequently developed, due to its brevity and flexibility for diversification. Aruncin B (<jats:bold>36<\/jats:bold>), together with 14 \u03b3\u2010alkylidenebutenolide analogues, were generated for biological evaluation.<\/jats:p>","DOI":"10.1002\/chem.201702949","type":"journal-article","created":{"date-parts":[[2017,8,17]],"date-time":"2017-08-17T03:43:16Z","timestamp":1502941396000},"page":"16525-16534","source":"Crossref","is-referenced-by-count":7,"title":["Aruncin B: Synthetic Studies, Structural Reassignment and Biological Evaluation"],"prefix":"10.1002","volume":"23","author":[{"given":"Aubert","family":"Ribaucourt","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Oxford, Chemistry Research Laboratory  Mansfield Road Oxford OX1 3TA UK"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Christopher","family":"Towers","sequence":"additional","affiliation":[{"name":"Department of Oncology University of Oxford, Old Road Campus Research Building  Oxford OX3 7DQ UK"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Laia","family":"Josa\u2010Culler\u00e9","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Oxford, Chemistry Research Laboratory  Mansfield Road Oxford OX1 3TA UK"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Frances","family":"Willenbrock","sequence":"additional","affiliation":[{"name":"Department of Oncology University of Oxford, Old Road Campus Research Building  Oxford OX3 7DQ UK"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Amber L.","family":"Thompson","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Oxford, Chemistry Research Laboratory  Mansfield Road Oxford OX1 3TA UK"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7201-9841","authenticated-orcid":false,"given":"David M.","family":"Hodgson","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Oxford, Chemistry Research Laboratory  Mansfield Road Oxford OX1 3TA UK"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2017,10,30]]},"reference":[{"doi-asserted-by":"publisher","key":"e_1_2_6_1_1","DOI":"10.1517\/14728222.2013.733001"},{"doi-asserted-by":"publisher","key":"e_1_2_6_2_1","DOI":"10.1016\/j.bmcl.2011.04.043"},{"doi-asserted-by":"publisher","key":"e_1_2_6_3_1","DOI":"10.1016\/j.bmcl.2011.12.023"},{"doi-asserted-by":"publisher","key":"e_1_2_6_4_1","DOI":"10.1021\/acs.orglett.6b02120"},{"unstructured":"\u00a0","key":"e_1_2_6_5_1"},{"doi-asserted-by":"publisher","key":"e_1_2_6_6_2","DOI":"10.1021\/ja00531a020"},{"doi-asserted-by":"publisher","key":"e_1_2_6_7_2","DOI":"10.1139\/v80-161"},{"doi-asserted-by":"publisher","key":"e_1_2_6_8_2","DOI":"10.1016\/0040-4039(95)02148-5"},{"doi-asserted-by":"publisher","key":"e_1_2_6_9_1","DOI":"10.1016\/j.tet.2007.03.066"},{"doi-asserted-by":"publisher","key":"e_1_2_6_10_1","DOI":"10.1016\/j.tet.2010.03.105"},{"doi-asserted-by":"publisher","key":"e_1_2_6_11_1","DOI":"10.1039\/B921600F"},{"doi-asserted-by":"publisher","key":"e_1_2_6_12_1","DOI":"10.1002\/anie.200704689"},{"doi-asserted-by":"publisher","key":"e_1_2_6_12_2","DOI":"10.1002\/ange.200704689"},{"doi-asserted-by":"publisher","key":"e_1_2_6_13_1","DOI":"10.1016\/j.tet.2007.05.007"},{"unstructured":"Low temperature single X-ray diffraction data were collected on the 3 5-dinitrobenzoate derivative of23using I19-1 at Diamond Light Source (\u03bb=0.6889\u2005\u00c5).[58]Raw frame data were reduced using the Xia2 pipeline;[59]the structure was solved with ShelXT[60]and refined using CRYSTALS[61]as per the Supporting Information (CIF). 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