Efficient synthesis of (R)-harmonine – the toxic principle of the multicolored Asian lady beetle (Harmonia axyridis)
| Autor: | Anita Masic, Nadja C. Nagel, Wilhelm Boland, Uta Schurigt |
|---|---|
| Rok vydání: | 2015 |
| Předmět: |
Stereochemistry
Proton Magnetic Resonance Spectroscopy Alkenes Biochemistry Esterase Mass Spectrometry Anti-Infective Agents Botany otorhinolaryngologic diseases Animals Carbon-13 Magnetic Resonance Spectroscopy Physical and Theoretical Chemistry Macrocyclic lactone chemistry.chemical_classification biology Chemistry Organic Chemistry Enantioselective synthesis Stereoisomerism Hydrogen-Ion Concentration Antimicrobial biology.organism_classification Harmonia axyridis Coleoptera (R)-harmonine Enantiomer Lactone |
| Zdroj: | Organic & Biomolecular Chemistry |
| ISSN: | 1477-0539 1477-0520 |
| DOI: | 10.1039/c5ob00461f |
| Popis: | A flexible synthetic route to (R)-harmonine ((R)-1), the toxic principle of the Asian lady beetle Harmonia axyridis (H. axyridis), via reductive olefination of the macrocyclic lactone (S)-5, is reported. High enantiomeric purity is achieved by enantioselective saponification of the lactone rac-5 with horse liver esterase. Minor modifications in the synthetic route give access to racemic and chiral harmonine (1), analogs and putative biosynthetic precursors. In addition, the antimicrobial activity of harmonine against Leishmania major (L. major) is demonstrated and provides the rationale for harmonine-based drug development against parasitic diseases. |
| Databáze: | OpenAIRE |
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