{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,17]],"date-time":"2026-07-17T23:03:49Z","timestamp":1784329429197,"version":"3.55.0"},"reference-count":29,"publisher":"Georg Thieme Verlag KG","issue":"12","funder":[{"name":"NIH","award":["CA042056"],"award-info":[{"award-number":["CA042056"]}]},{"DOI":"10.13039\/100000002","name":"National Institutes of Health","doi-asserted-by":"crossref","id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Synlett"],"published-print":{"date-parts":[[2026,7]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>A study of [bis(trifluoroacetoxy)iodo]benzene(PIFA)-mediated arylations of advanced model \u03b2-ketoesters and related substrates with vindoline for the total synthesis of vinblastine and related analogues is reported. The studies demonstrate the viability of the reaction in establishing the central C16\u2032\u2013C15 bond linking the upper velbanamine and lower vindoline subunits as well as define factors influencing formation of the natural C16\u2032 stereochemistry. Central to the potential of such an approach is the subsequent use of the \u03b2-ketoester-derived ketone for the divergent installation of a series of heterocycles, including the velbanamine indole required for vinblastine itself, from a common late-stage synthetic intermediate. Notably, such an approach represents the first that does not rely on a biomimetic coupling reaction, which necessarily requires an embedded indole in the velbanamine subunit precursor precluding indole replacements in the target structure.<\/jats:p>","DOI":"10.1055\/a-2843-2306","type":"journal-article","created":{"date-parts":[[2026,4,7]],"date-time":"2026-04-07T23:22:20Z","timestamp":1775604140000},"page":"1301-1306","source":"Crossref","is-referenced-by-count":0,"title":["PIFA-Mediated Coupling of Vindoline with \u03b2-Ketoesters and Related Model Velbanamine Precursors"],"prefix":"10.1055","volume":"37","author":[{"given":"Jiajun","family":"Zhang","sequence":"first","affiliation":[{"name":"Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nazanin","family":"Haddadpour","sequence":"first","affiliation":[{"name":"Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7764-0805","authenticated-orcid":false,"given":"Bin","family":"Cai","sequence":"additional","affiliation":[{"name":"Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3966-3317","authenticated-orcid":false,"given":"Dale L.","family":"Boger","sequence":"additional","affiliation":[{"name":"Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"194","published-online":{"date-parts":[[2026,4,7]]},"reference":[{"key":"ref1","first-page":"229","volume-title":"The Alkaloids","author":"N Neuss","year":"1990"},{"key":"ref2","doi-asserted-by":"crossref","first-page":"253","DOI":"10.1038\/nrc1317","volume":"4","author":"M A Jordan","year":"2004","journal-title":"Nat Rev Cancer"},{"key":"ref3","first-page":"94","volume":"17","author":"A Persidis","year":"1999","journal-title":"Biotechnology"},{"key":"ref4","doi-asserted-by":"crossref","first-page":"653","DOI":"10.1021\/ar500400w","volume":"48","author":"J E Sears","year":"2015","journal-title":"Acc Chem Res"},{"key":"ref5","doi-asserted-by":"crossref","first-page":"1428","DOI":"10.1021\/ol300173v","volume":"14","author":"E K Leggans","year":"2012","journal-title":"Org Lett"},{"key":"ref6","doi-asserted-by":"crossref","first-page":"628","DOI":"10.1021\/jm3015684","volume":"56","author":"E K Leggans","year":"2013","journal-title":"J Med Chem"},{"key":"ref7","doi-asserted-by":"crossref","first-page":"9691","DOI":"10.1073\/pnas.1611405113","volume":"113","author":"D W Carney","year":"2016","journal-title":"Proc Natl Acad Sci USA"},{"key":"ref8","doi-asserted-by":"crossref","first-page":"985","DOI":"10.1021\/ml400281w","volume":"4","author":"T J Barker","year":"2013","journal-title":"ACS Med Chem Lett"},{"key":"ref9","doi-asserted-by":"crossref","first-page":"7591","DOI":"10.1021\/acs.jmedchem.7b00958","volume":"60","author":"J C Lukesh","year":"2017","journal-title":"J Med Chem"},{"key":"ref10","doi-asserted-by":"crossref","first-page":"948","DOI":"10.1021\/ml200236a","volume":"2","author":"H Gotoh","year":"2011","journal-title":"ACS Med Chem Lett"},{"key":"ref11","first-page":"145","volume-title":"The Alkaloids","author":"H L Pearce","year":"1990"},{"key":"ref12","doi-asserted-by":"crossref","first-page":"4877","DOI":"10.1021\/jm201136z","volume":"55","author":"S A Hitchcock","year":"2012","journal-title":"J Med Chem"},{"key":"ref13","doi-asserted-by":"crossref","first-page":"1100","DOI":"10.1021\/ol400135n","volume":"15","author":"T C Turner","year":"2013","journal-title":"Org Lett"},{"key":"ref14","doi-asserted-by":"crossref","first-page":"495","DOI":"10.1021\/jacs.1c10971","volume":"144","author":"J Zhang","year":"2022","journal-title":"J Am Chem Soc"},{"key":"ref15","doi-asserted-by":"crossref","first-page":"14349","DOI":"10.1021\/jacs.9b06968","volume":"141","author":"B A Boon","year":"2019","journal-title":"J Am Chem Soc"},{"key":"ref16","doi-asserted-by":"crossref","first-page":"118","DOI":"10.1055\/a-1959-2088","volume":"56","author":"R M Gillard","year":"2024","journal-title":"Synthesis"},{"key":"ref17","volume-title":"Studies toward the Divergent Total Synthesis of Vinblastine and Heterocyclic Analogues Via a Novel Coupling Protocol","author":"J Zhang","year":"2019"},{"key":"ref18","doi-asserted-by":"crossref","first-page":"3684","DOI":"10.1021\/ja00088a003","volume":"116","author":"Y Kita","year":"1994","journal-title":"J Am Chem Soc"},{"key":"ref20","doi-asserted-by":"crossref","first-page":"2119","DOI":"10.1021\/jo902733f","volume":"75","author":"A A Zagulyaeva","year":"2010","journal-title":"J Org Chem"},{"key":"ref21","first-page":"77","volume-title":"In: The Alkaloids","author":"M E Kuehne","year":"1990"},{"key":"ref22","doi-asserted-by":"crossref","first-page":"7017","DOI":"10.1021\/ja00438a046","volume":"98","author":"N Langlois","year":"1976","journal-title":"J Am Chem Soc"},{"key":"ref23","doi-asserted-by":"crossref","first-page":"2858","DOI":"10.1002\/hlca.19760590824","volume":"59","author":"J P Kutney","year":"1976","journal-title":"Helv Chim Acta"},{"key":"ref24","doi-asserted-by":"crossref","first-page":"513","DOI":"10.1021\/jo00002a008","volume":"56","author":"M E Kuehne","year":"1991","journal-title":"J Org Chem"},{"key":"ref25","doi-asserted-by":"crossref","first-page":"1752","DOI":"10.1021\/jo00032a029","volume":"57","author":"W G Bornmann","year":"1992","journal-title":"J Org Chem"},{"key":"ref26","doi-asserted-by":"crossref","first-page":"8210","DOI":"10.1021\/ja00178a079","volume":"112","author":"P Magnus","year":"1990","journal-title":"J Am Chem Soc"},{"key":"ref27","doi-asserted-by":"crossref","first-page":"2137","DOI":"10.1021\/ja0177049","volume":"124","author":"S Yokoshima","year":"2002","journal-title":"J Am Chem Soc"},{"key":"ref28","doi-asserted-by":"crossref","first-page":"4904","DOI":"10.1021\/ja809842b","volume":"131","author":"H Ishikawa","year":"2009","journal-title":"J Am Chem Soc"},{"key":"ref29","doi-asserted-by":"crossref","first-page":"5530","DOI":"10.1039\/C6SC00932H","volume":"7","author":"Y Zhang","year":"2016","journal-title":"Chem Sci"},{"key":"ref30","doi-asserted-by":"crossref","first-page":"292","DOI":"10.1021\/acs.orglett.7b03694","volume":"20","author":"N Wang","year":"2018","journal-title":"Org Lett"}],"container-title":["Synlett"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/www.thieme-connect.de\/products\/ejournals\/pdf\/10.1055\/a-2843-2306.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,7,17]],"date-time":"2026-07-17T22:31:11Z","timestamp":1784327471000},"score":1,"resource":{"primary":{"URL":"http:\/\/www.thieme-connect.de\/DOI\/DOI?10.1055\/a-2843-2306"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,4,7]]},"references-count":29,"journal-issue":{"issue":"12","published-online":{"date-parts":[[2026,7,17]]},"published-print":{"date-parts":[[2026,7]]}},"URL":"https:\/\/doi.org\/10.1055\/a-2843-2306","archive":["Portico","CLOCKSS"],"relation":{},"ISSN":["0936-5214","1437-2096"],"issn-type":[{"value":"0936-5214","type":"print"},{"value":"1437-2096","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,4,7]]}}}