Structural Modifications at the C3 and C30 Positions of the Lupane Skeleton with Carbon-Centered Nucleophiles
Lupeol, a naturally occurring pentacyclic triterpenoid widely distributed in various medicinal plants, has attracted significant attention due to its diverse pharmacological properties. In this study, we report the synthesis and structural modification of 14 lupeol derivatives through selective func...
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MDPI AG
2025-07-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/30/15/3064 |
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| author | Davide Castiglione Gianfranco Fontana Laura Castoldi Vittorio Pace |
| author_facet | Davide Castiglione Gianfranco Fontana Laura Castoldi Vittorio Pace |
| author_sort | Davide Castiglione |
| collection | DOAJ |
| description | Lupeol, a naturally occurring pentacyclic triterpenoid widely distributed in various medicinal plants, has attracted significant attention due to its diverse pharmacological properties. In this study, we report the synthesis and structural modification of 14 lupeol derivatives through selective functionalizations at C3 and C30 positions of the lupane skeleton, via the sequential chemoselective introduction of carbonyl moieties and the addition of organometallics. Emphasis has been given to the stereoselective alkylation at C3 using a range of carbanions, including organolithiums, organomagnesiums and organoindiums. The C30 position was modified through oxidative pathways to introduce several functionalities. |
| format | Article |
| id | doaj-art-9af548bf82884bc59ceddd1665997dc9 |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-9af548bf82884bc59ceddd1665997dc92025-08-20T03:36:27ZengMDPI AGMolecules1420-30492025-07-013015306410.3390/molecules30153064Structural Modifications at the C3 and C30 Positions of the Lupane Skeleton with Carbon-Centered NucleophilesDavide Castiglione0Gianfranco Fontana1Laura Castoldi2Vittorio Pace3Department of Chemistry, University of Turin, Via P. Giuria 7, 10125 Turin, ItalyDipartimento di Scienze Biologiche, Chimiche e Farmaceutiche (STEBICEF), University of Palermo, Viale delle Scienze Ed. 17, 90128 Palermo, ItalyDepartment of Pharmaceutical Sciences, General and Organic Chemisty Section “A. Marchesini”, University of Milan, Via Venezian 21, 20133 Milan, ItalyDepartment of Chemistry, University of Turin, Via P. Giuria 7, 10125 Turin, ItalyLupeol, a naturally occurring pentacyclic triterpenoid widely distributed in various medicinal plants, has attracted significant attention due to its diverse pharmacological properties. In this study, we report the synthesis and structural modification of 14 lupeol derivatives through selective functionalizations at C3 and C30 positions of the lupane skeleton, via the sequential chemoselective introduction of carbonyl moieties and the addition of organometallics. Emphasis has been given to the stereoselective alkylation at C3 using a range of carbanions, including organolithiums, organomagnesiums and organoindiums. The C30 position was modified through oxidative pathways to introduce several functionalities.https://www.mdpi.com/1420-3049/30/15/3064lupeollupenonenatural substancesphytochemicalorganolithiumorganomagnesium |
| spellingShingle | Davide Castiglione Gianfranco Fontana Laura Castoldi Vittorio Pace Structural Modifications at the C3 and C30 Positions of the Lupane Skeleton with Carbon-Centered Nucleophiles Molecules lupeol lupenone natural substances phytochemical organolithium organomagnesium |
| title | Structural Modifications at the C3 and C30 Positions of the Lupane Skeleton with Carbon-Centered Nucleophiles |
| title_full | Structural Modifications at the C3 and C30 Positions of the Lupane Skeleton with Carbon-Centered Nucleophiles |
| title_fullStr | Structural Modifications at the C3 and C30 Positions of the Lupane Skeleton with Carbon-Centered Nucleophiles |
| title_full_unstemmed | Structural Modifications at the C3 and C30 Positions of the Lupane Skeleton with Carbon-Centered Nucleophiles |
| title_short | Structural Modifications at the C3 and C30 Positions of the Lupane Skeleton with Carbon-Centered Nucleophiles |
| title_sort | structural modifications at the c3 and c30 positions of the lupane skeleton with carbon centered nucleophiles |
| topic | lupeol lupenone natural substances phytochemical organolithium organomagnesium |
| url | https://www.mdpi.com/1420-3049/30/15/3064 |
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