{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,18]],"date-time":"2026-03-18T07:42:09Z","timestamp":1773819729161,"version":"3.50.1"},"reference-count":69,"publisher":"Wiley","issue":"25","license":[{"start":{"date-parts":[[2021,5,11]],"date-time":"2021-05-11T00:00:00Z","timestamp":1620691200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2021,5,11]],"date-time":"2021-05-11T00:00:00Z","timestamp":1620691200000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/100000928","name":"Welch Foundation","doi-asserted-by":"publisher","award":["F-0038"],"award-info":[{"award-number":["F-0038"]}],"id":[{"id":"10.13039\/100000928","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000057","name":"National Institute of General Medical Sciences","doi-asserted-by":"publisher","award":["RO1-GM093905"],"award-info":[{"award-number":["RO1-GM093905"]}],"id":[{"id":"10.13039\/100000057","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2021,6,14]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    The potent spliceosome modulator pladienolide\u2005B, which bears 10 stereogenic centers, is prepared in 10 steps (LLS). Asymmetric alcohol\u2010mediated carbonyl crotylations catalyzed by ruthenium and iridium that occur with\n                    <jats:italic>syn<\/jats:italic>\n                    \u2010 and\n                    <jats:italic>anti<\/jats:italic>\n                    \u2010diastereoselectivity, respectively, were used to form the C20\u2010C21 and C10\u2010C11 C\u2212C bonds.\n                  <\/jats:p>","DOI":"10.1002\/anie.202103845","type":"journal-article","created":{"date-parts":[[2021,4,1]],"date-time":"2021-04-01T13:26:08Z","timestamp":1617283568000},"page":"13923-13928","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":18,"title":["Total Synthesis of the Spliceosome Modulator Pladienolide\u2005B via Asymmetric Alcohol\u2010Mediated\n                    <i>syn<\/i>\n                    \u2010 and\n                    <i>anti<\/i>\n                    \u2010Diastereoselective Carbonyl Crotylation"],"prefix":"10.1002","volume":"60","author":[{"given":"Minjin","family":"Yoo","sequence":"first","affiliation":[{"name":"University of Texas at Austin Department of Chemistry  105 E 24th St. (A5300) Austin TX 78712-1167 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8418-9709","authenticated-orcid":false,"given":"Michael J.","family":"Krische","sequence":"additional","affiliation":[{"name":"University of Texas at Austin Department of Chemistry  105 E 24th St. (A5300) Austin TX 78712-1167 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2021,5,11]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"For isolation and structure determination of pladienolides\u2005A\u2013G see:"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.57.173"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.57.180"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1038\/ja.2007.49"},{"key":"e_1_2_2_5_1","unstructured":"For isolation and structure determination (via total synthesis) of FD-895 see:"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.47.1395"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol3023006"},{"key":"e_1_2_2_8_1","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.57.188"},{"key":"e_1_2_2_9_1","doi-asserted-by":"publisher","DOI":"10.1038\/nchembio.2007.16"},{"key":"e_1_2_2_10_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5NP00110B"},{"key":"e_1_2_2_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molcel.2018.03.011"},{"key":"e_1_2_2_12_1","unstructured":"\u00a0"},{"key":"e_1_2_2_13_2","unstructured":"ClinicalTrials.gov Identifier: NCT00499499;"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1007\/s10637-013-0046-5"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1158\/1078-0432.CCR-13-2461"},{"key":"e_1_2_2_16_1","unstructured":"\u00a0"},{"key":"e_1_2_2_17_2","unstructured":"ClinicalTrials.gov Identifier: NCT02841540;"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1038\/nm.4493"},{"key":"e_1_2_2_19_1","unstructured":"For prior total syntheses of pladienolide\u2005B and 6-deoxypladienolide\u2005D see:"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200604997"},{"key":"e_1_2_2_20_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200604997"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol301886g"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol401458d"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201301468"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol502556c"},{"key":"e_1_2_2_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.xcrp.2020.100277"},{"key":"e_1_2_2_26_1","unstructured":"For the semi-synthesis of E7107 see:"},{"key":"e_1_2_2_27_2","unstructured":"\u201cPhysiologically Active Substances\u201d:Y.Kotake J.Niijima Y.Fukuda R. M.Kanada T.Nakashima M.Yoshida T.Tsuchida(Eisai R&D Management Co. Ltd. Merican Corporation) United States patent US 7 550 503 2009Jun 23. For the synthesis of H3B-8800 see:"},{"key":"e_1_2_2_28_2","unstructured":"\u201cA Solid State Form of Pladienolide Pyridine Compounds and Methods of Use\u201d:G. F.Keaney J.Wang B.Gerard K.Arai X.Liu G. Z.Zheng K.Kira P.Tibitma-Haisoon S.Prajapati Y.Kotake M. R.Kanada(Eisai R&D Management Co. Ltd.) International patent WO 2017\/087667 2017May 26."},{"key":"e_1_2_2_29_1","unstructured":"For syntheses of pladienolide and FD-895 substructures see:"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2007.06.094"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol800946x"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol201464m"},{"key":"e_1_2_2_33_1","unstructured":"For selected reviews highlighting recent advances in type I polyketide total synthesis see:"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3np70076c"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b02019"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8CS00399H"},{"key":"e_1_2_2_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201812982"},{"key":"e_1_2_2_37_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201812982"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9NP00070D"},{"key":"e_1_2_2_39_1","unstructured":"For selected reviews on alcohol-mediated carbonyl allylation and propargylation via metal-catalyzed hydrogen auto-transfer see:"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.7b00308"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.201801121"},{"key":"e_1_2_2_42_1","unstructured":"For ruthenium-catalyzedsyn-crotylation mediated by butadiene see:"},{"key":"e_1_2_2_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja311208a"},{"key":"e_1_2_2_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja4008722"},{"key":"e_1_2_2_45_1","unstructured":"For iridium-catalyzedanti-crotylation mediated by \u03b1-methyl allyl acetate see:"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja808857w"},{"key":"e_1_2_2_46_3","doi-asserted-by":"publisher","DOI":"10.1021\/jo200068q"},{"key":"e_1_2_2_47_1","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.52.1989"},{"key":"e_1_2_2_48_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b01776"},{"key":"e_1_2_2_49_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja972272g"},{"key":"e_1_2_2_50_1","unstructured":"\u00a0"},{"key":"e_1_2_2_51_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39780000876"},{"key":"e_1_2_2_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo01311a037"},{"key":"e_1_2_2_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00397a053"},{"key":"e_1_2_2_54_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2003.08.065"},{"key":"e_1_2_2_55_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b00883"},{"key":"e_1_2_2_56_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-1992-21404"},{"key":"e_1_2_2_57_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja954126l"},{"key":"e_1_2_2_58_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201901927"},{"key":"e_1_2_2_58_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201901927"},{"key":"e_1_2_2_59_1","unstructured":"Related esterificationsen routeto pladienolide\u2005B have involved compounds in which the C7 hydroxyl is protected (see references\u2005[9b] and [9c])."},{"key":"e_1_2_2_60_1","unstructured":"\u00a0"},{"key":"e_1_2_2_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00333a041"},{"key":"e_1_2_2_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol302898h"},{"key":"e_1_2_2_63_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol990947"},{"key":"e_1_2_2_64_1","doi-asserted-by":"publisher","DOI":"10.1039\/C3CC48670B"},{"key":"e_1_2_2_65_1","unstructured":"While our manuscript was under review Rhoades et\u2005al. reported total syntheses of pladienolide\u2005B and H3B-8800 using our method for enantioselective iridium-catalyzedanti-crotylation (https:\/\/doi.org\/10.1021\/jacs.1c01135). 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