Plant-Derived Triterpenoid Functionalization: Synthesis of α-Acyloxycarboxamides
The application of isocyanide-based multicomponent reactions (IMCRs) for triterpenoid functionalization has been little reported. Triterpenoids and their derivatives are an important class of natural products of interest in medicinal chemistry due to their potential applications as antibacterial, an...
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MDPI AG
2023-11-01
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| author | Fidel Rodriguez-Lopez Edgar G. Rodríguez-García Hugo A. García-Gutiérrez Rocío Gámez-Montaño |
| author_facet | Fidel Rodriguez-Lopez Edgar G. Rodríguez-García Hugo A. García-Gutiérrez Rocío Gámez-Montaño |
| author_sort | Fidel Rodriguez-Lopez |
| collection | DOAJ |
| description | The application of isocyanide-based multicomponent reactions (IMCRs) for triterpenoid functionalization has been little reported. Triterpenoids and their derivatives are an important class of natural products of interest in medicinal chemistry due to their potential applications as antibacterial, antifungal, and cytotoxic agents. Herein, we describe the use of ethanol as a solvent in the Passerini reaction for the functionalization of masticadienonic acid isolated from fruits and peduncles of <i>P. mexicana</i>. A small series of α-acyloxycarboxamides was synthesized with moderate to good overall yields of 33 to 57%, evaluating and extending the scope of the aldehyde component. |
| format | Article |
| id | doaj-art-cbf6eb4459b54e88a1eb92cd5b433b0e |
| institution | DOAJ |
| issn | 2673-4583 |
| language | English |
| publishDate | 2023-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Chemistry Proceedings |
| spelling | doaj-art-cbf6eb4459b54e88a1eb92cd5b433b0e2025-08-20T02:55:44ZengMDPI AGChemistry Proceedings2673-45832023-11-0114110210.3390/ecsoc-27-16061Plant-Derived Triterpenoid Functionalization: Synthesis of α-AcyloxycarboxamidesFidel Rodriguez-Lopez0Edgar G. Rodríguez-García1Hugo A. García-Gutiérrez2Rocío Gámez-Montaño3Instituto de Investigaciones Químico Biológicas, Universidad Michoacana de San Nicolás de Hidalgo, Edificio B-1, Cd. Universitaria, Morelia 58030, MexicoDepartamento de Química, Universidad de Guanajuato, Noria Alta S/N, Col. Noria Alta, Guanajuato 36050, MexicoInstituto de Investigaciones Químico Biológicas, Universidad Michoacana de San Nicolás de Hidalgo, Edificio B-1, Cd. Universitaria, Morelia 58030, MexicoDepartamento de Química, Universidad de Guanajuato, Noria Alta S/N, Col. Noria Alta, Guanajuato 36050, MexicoThe application of isocyanide-based multicomponent reactions (IMCRs) for triterpenoid functionalization has been little reported. Triterpenoids and their derivatives are an important class of natural products of interest in medicinal chemistry due to their potential applications as antibacterial, antifungal, and cytotoxic agents. Herein, we describe the use of ethanol as a solvent in the Passerini reaction for the functionalization of masticadienonic acid isolated from fruits and peduncles of <i>P. mexicana</i>. A small series of α-acyloxycarboxamides was synthesized with moderate to good overall yields of 33 to 57%, evaluating and extending the scope of the aldehyde component.https://www.mdpi.com/2673-4583/14/1/102triterpenoidIMCRPasserini-3CRα-acyloxycarboxamide |
| spellingShingle | Fidel Rodriguez-Lopez Edgar G. Rodríguez-García Hugo A. García-Gutiérrez Rocío Gámez-Montaño Plant-Derived Triterpenoid Functionalization: Synthesis of α-Acyloxycarboxamides Chemistry Proceedings triterpenoid IMCR Passerini-3CR α-acyloxycarboxamide |
| title | Plant-Derived Triterpenoid Functionalization: Synthesis of α-Acyloxycarboxamides |
| title_full | Plant-Derived Triterpenoid Functionalization: Synthesis of α-Acyloxycarboxamides |
| title_fullStr | Plant-Derived Triterpenoid Functionalization: Synthesis of α-Acyloxycarboxamides |
| title_full_unstemmed | Plant-Derived Triterpenoid Functionalization: Synthesis of α-Acyloxycarboxamides |
| title_short | Plant-Derived Triterpenoid Functionalization: Synthesis of α-Acyloxycarboxamides |
| title_sort | plant derived triterpenoid functionalization synthesis of α acyloxycarboxamides |
| topic | triterpenoid IMCR Passerini-3CR α-acyloxycarboxamide |
| url | https://www.mdpi.com/2673-4583/14/1/102 |
| work_keys_str_mv | AT fidelrodriguezlopez plantderivedtriterpenoidfunctionalizationsynthesisofaacyloxycarboxamides AT edgargrodriguezgarcia plantderivedtriterpenoidfunctionalizationsynthesisofaacyloxycarboxamides AT hugoagarciagutierrez plantderivedtriterpenoidfunctionalizationsynthesisofaacyloxycarboxamides AT rociogamezmontano plantderivedtriterpenoidfunctionalizationsynthesisofaacyloxycarboxamides |