Structure and Synthesis of Vindolicine and Derivatives
Abstract: This article describes the reaction of vindoline with formaldehyde and trimethyl orthoformate to prepare vindolicine, tris‐vindolicinyl methane and higher molecular weight homologues. The synthesis of 10‐formyl 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‐formyl vindoline, 10‐(1’‐(but‐1’‐en‐3’‐one))‐vindoline) by X‐ray crystallography. Depending on the substitution and on the absence of axes of symmetry, the NMR spectra displayed non‐equivalent spin systems for the vindoline moieties. The dimer formed from the double condensation of 10‐formyl vindoline with acetone showed cytotoxic activity in the micromolar range.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Structure and Synthesis of Vindolicine and Derivatives ; day:26 ; month:02 ; year:2024 ; extent:9
Chemistry & biodiversity ; (26.02.2024) (gesamt 9)
- Creator
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Asia
Sammer, Yousuf
Vendier, Laure
Massiot, Georges
- DOI
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10.1002/cbdv.202301928
- URN
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urn:nbn:de:101:1-2024022714192066266504
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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14.08.2025, 10:51 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Asia
- Sammer, Yousuf
- Vendier, Laure
- Massiot, Georges
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