Regiospecificity in the reaction of 2,3-dichloronaphthazarins with azide anions. Synthesis of echinamine A—a metabolite produced by the sea urchin Scaphechinus mirabilis

It was found that 6-hydroxy- and 6-alkoxy-2,3-dichloronaphthazarins react smoothly with sodium azide in methanol to produce the corresponding 2-azido derivatives as single regioisomers. We have explored the utility of this reaction for the synthesis of echinamine A (3-amino-7-ethyl-2,5,6,8-tetrahydr...

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Bibliographic Details
Published in:Tetrahedron letters 2006-02, Vol.47 (9), p.1385-1387
Main Authors: Pokhilo, Nataly D., Yakubovskaya, Alla Ya, Denisenko, Vladimir A., Anufriev, Victor Ph
Format: Article
Language:English
Subjects:
2,3-Dichloronaphthazarins
3-Amino-7-ethyl-2,5,6,8-tetrahydroxy-1,4-naphthoquinone
Azido group
Echinamine A
Regiospecificity of substitution
Sea urchin, Scaphechinus mirabilis (Agassiz)
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Summary:It was found that 6-hydroxy- and 6-alkoxy-2,3-dichloronaphthazarins react smoothly with sodium azide in methanol to produce the corresponding 2-azido derivatives as single regioisomers. We have explored the utility of this reaction for the synthesis of echinamine A (3-amino-7-ethyl-2,5,6,8-tetrahydroxy-1,4-naphthoquinone)—the first marine aminated hydroxynaphthazarin, a metabolite of the sea urchin Scaphechinus mirabilis (Agassiz).
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.12.109