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The key synthetic features include Shiina macrolactonization to assemble the 14\u2010membered macrocyclic core, Wittig or Still\u2010Gennari olefination and selective reduction of propargylic alcohol to construct the <jats:italic>E<\/jats:italic>\u2010 or <jats:italic>Z<\/jats:italic>\u2010olefins. Cross metathesis was also highlighted as an efficient tool to forge the formation of <jats:italic>E<\/jats:italic>\u2010olefin. The three synthetic macrolides were evaluated for their cytotoxic activity against three human cancer cell lines as well as for inhibitory effect on CFTR\u2010mediated chloride secretion in human intestinal epithelial (T84) cells. Mutolide displayed significant cytotoxic activity against HCT116 colon cancer cells with an IC<jats:sub>50<\/jats:sub> of \u223c12\u2005\u03bcM as well as a potent CTFR inhibitory effect with an IC<jats:sub>50<\/jats:sub> value of \u223c1\u2005\u03bcM.<\/jats:p>","DOI":"10.1002\/asia.202200329","type":"journal-article","created":{"date-parts":[[2022,6,21]],"date-time":"2022-06-21T14:07:32Z","timestamp":1655820452000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Total Synthesis and Biological Evaluation of Mutolide and Analogues"],"prefix":"10.1002","volume":"17","author":[{"given":"Aticha","family":"Thiraporn","sequence":"first","affiliation":[{"name":"Division of Physical Science and Center of Excellence for Innovation in Chemistry, Faculty of Science Prince of Songkla University  Hat Yai Songkhla 90110 Thailand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nongluk","family":"Saikachain","sequence":"additional","affiliation":[{"name":"Chakri Naruebodindra Medical Institute Faculty of Medicine Ramathibodi Hospital Mahidol University  Bang Pla, Bang Pli Samut Prakan 10540 Thailand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rungtiwa","family":"Khumjiang","sequence":"additional","affiliation":[{"name":"Chakri Naruebodindra Medical Institute Faculty of Medicine Ramathibodi Hospital Mahidol University  Bang Pla, Bang Pli Samut Prakan 10540 Thailand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6849-6637","authenticated-orcid":false,"given":"Chatchai","family":"Muanprasat","sequence":"additional","affiliation":[{"name":"Chakri Naruebodindra Medical Institute Faculty of Medicine Ramathibodi Hospital Mahidol University  Bang Pla, Bang Pli Samut Prakan 10540 Thailand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1110-8119","authenticated-orcid":false,"given":"Kwanruthai","family":"Tadpetch","sequence":"additional","affiliation":[{"name":"Division of Physical Science and Center of Excellence for Innovation in Chemistry, Faculty of Science Prince of Songkla University  Hat Yai Songkhla 90110 Thailand"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,7,6]]},"reference":[{"key":"e_1_2_6_1_1","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1517\/13543784.4.2.65"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.2165\/00003495-200161040-00003"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2019.111662"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.3390\/md19040180"},{"key":"e_1_2_6_6_1","first-page":"281","volume":"2","author":"McGuire J. 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