Total Synthesis of (−)-Aspergilazine A
| Autor: | Jonathan Sperry, Emily M. Boyd |
|---|---|
| Rok vydání: | 2014 |
| Předmět: |
Molecular Structure
Stereochemistry Ligand Dimer Organic Chemistry Total synthesis Marine Biology Stereoisomerism Dipeptides Ligands Biochemistry Catalysis Indole Alkaloids Stereocenter chemistry.chemical_compound Alkaloids Aspergillus chemistry XPhos Brevianamide Epimer Physical and Theoretical Chemistry Palladium |
| Zdroj: | Organic Letters. 16:5056-5059 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | The total synthesis of (-)-aspergilazine A, an alkaloid possessing a rare N1' to C6 bisindole bond, is described. A palladium-catalyzed N-arylation was used to selectively install the N1'-C6 bond in the presence of three other possible arylation sites. The ligand XPhos displayed a unique capability to efficiently carry out the N-arylation while simultaneously suppressing epimerization of the sensitive C9 stereocenters. This total synthesis has confirmed that aspergilazine A is a dimer of brevianamide F. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|