{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,14]],"date-time":"2025-11-14T04:02:11Z","timestamp":1763092931958,"version":"build-2065373602"},"reference-count":35,"publisher":"Wiley","issue":"4","license":[{"start":{"date-parts":[[2024,2,26]],"date-time":"2024-02-26T00:00:00Z","timestamp":1708905600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry &amp; Biodiversity"],"published-print":{"date-parts":[[2024,4]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>This article describes the reaction of vindoline with formaldehyde and trimethyl orthoformate to prepare vindolicine, tris\u2010vindolicinyl methane and higher molecular weight homologues. The synthesis of 10\u2010formyl vindoline as an intermediate allowed further exploration of its chemistry, in particular the reaction with acetone which yielded a symmetrical dimer, which was further reacted with vindoline to give molecules containing three and four vindoline units. These molecules were characterized by NMR and for some of them (vindolicine, 10\u2010formyl vindoline, 10\u2010(1\u2019\u2010(but\u20101\u2019\u2010en\u20103\u2019\u2010one))\u2010vindoline) by X\u2010ray crystallography. Depending on the substitution and on the absence of axes of symmetry, the NMR spectra displayed non\u2010equivalent spin systems for the vindoline moieties. The dimer formed from the double condensation of 10\u2010formyl vindoline with acetone showed cytotoxic activity in the micromolar range.<\/jats:p>","DOI":"10.1002\/cbdv.202301928","type":"journal-article","created":{"date-parts":[[2024,2,26]],"date-time":"2024-02-26T23:11:28Z","timestamp":1708989088000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Structure and Synthesis of Vindolicine and Derivatives"],"prefix":"10.1002","volume":"21","author":[{"ORCID":"https:\/\/orcid.org\/0009-0005-9899-0843","authenticated-orcid":false,"family":"Asia","sequence":"first","affiliation":[{"name":"H. E. J. Research Institute of Chemistry International Center for Chemical and Biological Sciences University of Karachi  Karachi 75270 Sindh Pakistan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8870-3581","authenticated-orcid":false,"given":"Yousuf","family":"Sammer","sequence":"additional","affiliation":[{"name":"H. E. J. Research Institute of Chemistry International Center for Chemical and Biological Sciences University of Karachi  Karachi 75270 Sindh Pakistan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7111-9258","authenticated-orcid":false,"given":"Laure","family":"Vendier","sequence":"additional","affiliation":[{"name":"UPR CNRS 8241 Laboratoire de Chimie de Coordination  205 Route de Narbonne 31077 Toulouse Cedex 04 France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3507-8559","authenticated-orcid":false,"given":"Georges","family":"Massiot","sequence":"additional","affiliation":[{"name":"Institut de Chimie Mol\u00e9culaire de Reims UMR CNRS 7312 Universit\u00e9 Reims-Champagne-Ardenne UFR Sciences, BP 1039, CEDEX 2  51687 Reims France"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2024,2,26]]},"reference":[{"key":"e_1_2_9_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/jps.2600500508"},{"key":"e_1_2_9_2_1","unstructured":"M. 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