Synthetic study of cnicin: Synthesis of the side chain and its esterification
| Autor: | Miho Tanigawa, Shuhei Narita, Manami Kurita, Toyonobu Usuki |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
Germacranolide
chemistry.chemical_classification biology 010405 organic chemistry Stereochemistry Carboxylic acid Organic Chemistry Primary alcohol Trypanosoma brucei 010402 general chemistry Sesquiterpene lactone biology.organism_classification 01 natural sciences Biochemistry Cnicin 0104 chemical sciences chemistry.chemical_compound chemistry parasitic diseases Drug Discovery Side chain Organic chemistry Moiety |
| Zdroj: | Tetrahedron Letters. 57:5899-5901 |
| ISSN: | 0040-4039 |
| Popis: | Cnicin is a germacranolide sesquiterpene lactone that possesses potent inhibitory activity against the protozoan parasite Trypanosoma brucei, which causes human African trypanosomiasis (HAT). Although cnicin has an interesting structure and attractive biological activity, synthetic studies of cnicin have not yet been reported. This report describes the synthesis of the protected side chain carboxylic acid moiety at C8 of cnicin via two routes starting from l-ascorbic acid. In addition, esterification between the synthetic side chain and salonitenolide derivative, which can be achieved via hydrolysis of cnicin and protection of the primary alcohol, was conducted. Thus, a semi-synthesis of cnicin was achieved. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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