Unexpected conversion of echinochrome to brominated spinochrome D. Synthesis of 2-amino-3,6,7-trihydroxynaphthazarin produced by the sea urchins Strongylocentrotus nudus and Psammechinus miliaris
| Autor: | Vyacheslav V. Makhankov, Ksenia L. Borisova, Victor Ph. Anufriev, N. D. Pokhilo, Galina I. Melman |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
biology
010405 organic chemistry Chemistry Strongylocentrotus nudus Stereochemistry Metabolite Organic Chemistry Total synthesis Psammechinus miliaris Bromine atom biology.organism_classification 01 natural sciences Biochemistry 0104 chemical sciences Spinochrome D 010404 medicinal & biomolecular chemistry chemistry.chemical_compound Drug Discovery |
| Zdroj: | Tetrahedron Letters. 57:736-738 |
| ISSN: | 0040-4039 |
| Popis: | Two approaches to the total synthesis of 2-amino-3,6,7-trihydroxynaphthazarin, a metabolite of the sea urchins Strongylocentrotus nudus and Psammechinus miliaris are described. The first was based on the conversion of 2,3-dichloro-6,7-dimethoxynaphthazarin into the corresponding 3-hydroxy-2-nitro derivative and subsequent reduction to give 2-amino-3-hydroxy-6,7-dimethoxynaphthazarin. The basis for the second method was the conversion of echinochrome into brominated spinochrome D and the introduction of an amino group via direct substitution of the bromine atom by an azido group. |
| Databáze: | OpenAIRE |
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