{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,25]],"date-time":"2026-08-25T15:32:40Z","timestamp":1787671960060,"version":"build-2736575974"},"reference-count":56,"publisher":"Wiley","issue":"32","license":[{"start":{"date-parts":[[2026,7,2]],"date-time":"2026-07-02T00:00:00Z","timestamp":1782950400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,7,2]],"date-time":"2026-07-02T00:00:00Z","timestamp":1782950400000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2026,8,24]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Herein, we report the synthesis of the three key fragments of the macrolide antibiotic (+)\u2010neosorangicin A, a compound exhibiting potent activity against multiple pathogens. The tetrahydropyran unit (THP) was prepared via stereocontrolled Brown crotylation, followed by hydroboration and epoxide\u2010opening\/cyclization steps. Subsequent coupling with the known dioxabicyclo[3.2.1]octane fragment (BCO) via Grubbs metathesis furnished the THP\u2013BCO key intermediate on a gram scale. This intermediate was further transformed into an\n                    <jats:italic>E<\/jats:italic>\n                    \u2010vinyl iodide for a late\u2010stage Stille coupling with the dihydropyran fragment (DHP), incorporating a shortened side chain relative to (+)\u2010sorangicin A and bearing a secondary alcohol. This fragment was synthesized via 1,2\u2010addition to a dihydropyran\u2010methyl ketone followed by dehydration. Subsequent functional group manipulations enabled access to a phosphonate intermediate, which was converted into a stannylated\n                    <jats:italic>Z<\/jats:italic>\n                    ,\n                    <jats:italic>Z<\/jats:italic>\n                    \u2010diene via Ando olefination. The Stille coupling between the THP\u2013BCO and the DHP fragments provided the carbon skeleton of the natural product and was confirmed by a relay approach using isolated (+)\u2010neosorangicin A. This work establishes a selective route to the key building blocks, providing a foundation for the convergent total synthesis of (+)\u2010neosorangicin A and a proof of concept via a relay approach.\n                  <\/jats:p>","DOI":"10.1002\/chem.71360","type":"journal-article","created":{"date-parts":[[2026,7,2]],"date-time":"2026-07-02T16:29:57Z","timestamp":1783009797000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Relay Approach: A Convergent Synthesis of Key Fragments en route to (+)\u2010Neosorangicin A"],"prefix":"10.1002","volume":"32","author":[{"ORCID":"https:\/\/orcid.org\/0009-0002-8667-5895","authenticated-orcid":false,"given":"Marvin","family":"Wenninger","sequence":"first","affiliation":[{"name":"Institut f\u00fcr Chemie Otto\u2010von\u2010Guericke\u2010Universit\u00e4t Magdeburg  Magdeburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maxim","family":"Munt","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Chemie Otto\u2010von\u2010Guericke\u2010Universit\u00e4t Magdeburg  Magdeburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Le","family":"Chang","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Chemie Otto\u2010von\u2010Guericke\u2010Universit\u00e4t Magdeburg  Magdeburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rositsa","family":"Stoykova","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Chemie Otto\u2010von\u2010Guericke\u2010Universit\u00e4t Magdeburg  Magdeburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Roberto","family":"Ojcius","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Chemie Otto\u2010von\u2010Guericke\u2010Universit\u00e4t Magdeburg  Magdeburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Oliver","family":"Spie\u00df","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Chemie Otto\u2010von\u2010Guericke\u2010Universit\u00e4t Magdeburg  Magdeburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1462-7501","authenticated-orcid":false,"given":"Dieter","family":"Schinzer","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Chemie Otto\u2010von\u2010Guericke\u2010Universit\u00e4t Magdeburg  Magdeburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,7,2]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)95117-7"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.6c00056"},{"key":"e_1_2_6_4_1","unstructured":"R.M\u00fcller N.Zaburannyi J.Herrmann R.Jansen K.Mohr andS.Karwehl (2020) EP3 498 714B1."},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1038\/sj.emboj.7600499"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.2013706117"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol051119l"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja906115a"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2011.09.035"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol802942j"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol049644s"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol201920j"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol061339e"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b02729"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-2004-835661"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0033-1340739"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0033-1340182"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.5012\/bkcs.2008.29.9.1661"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3ob40985f"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.6b01743"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200902999"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2018.01.036"},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201101549"},{"key":"e_1_2_6_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2015.09.037"},{"key":"e_1_2_6_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2009.06.035"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.198919890124"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00262a017"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00279a042"},{"key":"e_1_2_6_29_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)85574-5"},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja504228p"},{"key":"e_1_2_6_31_1","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19990503)38:9<1263::AID-ANIE1263>3.0.CO;2-2"},{"key":"e_1_2_6_32_1","doi-asserted-by":"publisher","DOI":"10.1080\/07328303.2015.1115514"},{"key":"e_1_2_6_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)77276-5"},{"key":"e_1_2_6_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo972146v"},{"key":"e_1_2_6_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol035227o"},{"key":"e_1_2_6_36_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-1998-1570"},{"key":"e_1_2_6_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol062167o"},{"key":"e_1_2_6_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja5105602"},{"key":"e_1_2_6_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c00168"},{"key":"e_1_2_6_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.4c00737"},{"key":"e_1_2_6_41_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)85909-2"},{"key":"e_1_2_6_42_1","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(95)00726-S"},{"key":"e_1_2_6_43_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2003.08.095"},{"key":"e_1_2_6_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol025553o"},{"key":"e_1_2_6_45_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)01840-8"},{"key":"e_1_2_6_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol990723r"},{"key":"e_1_2_6_47_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)79590-6"},{"key":"e_1_2_6_48_1","doi-asserted-by":"publisher","DOI":"10.1039\/a909898d"},{"key":"e_1_2_6_49_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)81981-5"},{"key":"e_1_2_6_50_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo8006539"},{"key":"e_1_2_6_51_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja028186k"},{"key":"e_1_2_6_52_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol051584i"},{"key":"e_1_2_6_53_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200701677"},{"key":"e_1_2_6_54_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(99)00956-9"},{"key":"e_1_2_6_55_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01143a007"},{"key":"e_1_2_6_56_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00349a037"},{"key":"e_1_2_6_57_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-1994-22755"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.71360","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.71360","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.71360","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,25]],"date-time":"2026-08-25T15:11:18Z","timestamp":1787670678000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.71360"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,7,2]]},"references-count":56,"journal-issue":{"issue":"32","published-print":{"date-parts":[[2026,8,24]]}},"alternative-id":["10.1002\/chem.71360"],"URL":"https:\/\/doi.org\/10.1002\/chem.71360","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,7,2]]},"assertion":[{"value":"2026-04-27","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-06-20","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-07-02","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e71360"}}