Structural Modifications at the C3 and C30 Positions of the Lupane Skeleton with Carbon-Centered Nucleophiles.

Davide Castiglione, Gianfranco Fontana, Laura Castoldi, Vittorio Pace

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Article in Molecules (Basel, Switzerland), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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5 · Who and what money

Authors and funding

4 authors.

Davide CastiglioneDepartment of Chemistry, University of Turin, Via P. Giuria 7, 10125 Turin, Italy.

Gianfranco FontanaDipartimento di Scienze Biologiche, Chimiche e Farmaceutiche (STEBICEF), University of Palermo, Viale delle Scienze Ed. 17, 90128 Palermo, Italy.

Laura CastoldiDepartment of Pharmaceutical Sciences, General and Organic Chemisty Section "A. Marchesini", University of Milan, Via Venezian 21, 20133 Milan, Italy.

Vittorio PaceDepartment of Chemistry, University of Turin, Via P. Giuria 7, 10125 Turin, Italy.ORCID 0000-0003-3037-5930

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

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.

Indexed as

carbenoidhomologationlupenonelupeolnatural substancesorganoindiumorganolithiumorganomagnesiumphytochemical

Identifiers

PMID40807239

DOI10.3390/molecules30153064

PMCPMC12348400

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.