Divergent Synthesis of Natural Benzyl Salicylate and Benzyl Gentisate Glucosides
| Autor: | Markus D. Kärkäs, Elena V. Stepanova, David L Avetyan, Andrey Shatskiy, Dariya S Nazarova, Dariya D Fedorova, M. L. Belyanin |
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| Rok vydání: | 2020 |
| Předmět: |
Pharmacology
Benzyl salicylate chemistry.chemical_classification Molecular Structure Gentisates Organic Chemistry Pharmaceutical Science Total synthesis Glycoside Phenolic acid Salicylates Analytical Chemistry chemistry.chemical_compound Populus Complementary and alternative medicine chemistry Acetylation Yield (chemistry) Benzyl Compounds Drug Discovery Molecular Medicine Organic chemistry Glycosides Gentisic acid Divergent synthesis |
| Zdroj: | Journal of Natural Products. 83:3173-3180 |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/acs.jnatprod.0c00838 |
| Popis: | Herein is reported the first total synthesis of benzyl salicylate and benzyl gentisate glucosides present in various plant species, in particular the Salix genus, such as Populus balsamifera and P. trichocarpa. The method permits the synthesis of several natural phenolic acid derivatives and their glucosides starting from salicylic or gentisic acid. The divergent approach afforded access to three different acetylated glucosides from a common synthetic intermediate. The key step in the total synthesis of naturally occurring glycosides-the selective deacetylation of the sugar moiety-was achieved in the presence of a labile benzyl ester group by employing mild deacetylation conditions. The protocol permitted synthesis of trichocarpine (4 steps, 40% overall yield), isotrichocarpine (3 steps, 51% overall yield), trichoside (6 steps, 40% overall yield), and deoxytrichocarpine (3 steps, 42% overall yield) for the first time (>95% purity). Also, the optimized mild deacetylation conditions allowed synthesis of 2-O-acetylated derivatives of all four glycosides (5-17% overall yield, 90-95% purity), which are rare plant metabolites. |
| Databáze: | OpenAIRE |
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