A general strategy for the synthesis of indoloquinolizine alkaloids via a cyanide-catalyzed imino-Stetter reaction
| Autor: | Cheol Hong Cheon, Eunjoon Park |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
Aldimine Cyanides Molecular Structure 010405 organic chemistry Cyanide Carboxylic acid Organic Chemistry Stetter reaction Alcohol 010402 general chemistry 01 natural sciences Biochemistry Catalysis 0104 chemical sciences chemistry.chemical_compound Alkaloids chemistry Intramolecular force Moiety Organic chemistry Imines Physical and Theoretical Chemistry Quinolizines |
| Zdroj: | Organic & Biomolecular Chemistry. 15:10265-10275 |
| ISSN: | 1477-0539 1477-0520 |
| DOI: | 10.1039/c7ob02691a |
| Popis: | A new strategy applicable to the synthesis of indoloquinolizine natural products has been developed. A cyanide-catalyzed intramolecular imino-Stetter reaction of aldimines, derived from 2-aminocinnamic acid derivatives and 2-pyridinecarboxaldehydes, provided indole-3-acetic acid derivatives bearing a pyridyl ring at the 2-position. Reduction of the carboxylic acid moiety to an alcohol followed by activation of the resulting alcohol with Tf2O or TsCl generated indoloquinolizinium salts, which were utilized as precursors for indoloquinolizine natural products. The advantage of this protocol was successfully demonstrated in the total syntheses of arborescidine A and nauclefidine. |
| Databáze: | OpenAIRE |
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