Enantiocontrolled Synthesis of a Tetracyclic Aminal Corresponding to the Core Subunit of Diazonamide A
| Autor: | Edwin Vedejs, Gorka Peris |
|---|---|
| Rok vydání: | 2015 |
| Předmět: |
inorganic chemicals
Stereochemistry organic chemicals Protein subunit Organic Chemistry Molecular Conformation Substituent Diastereomer Stereoisomerism Ether Ring (chemistry) Heterocyclic Compounds 4 or More Rings chemistry.chemical_compound chemistry Carboxylation Aminal heterocyclic compounds Oxindole Oxazoles |
| Zdroj: | The Journal of Organic Chemistry. 80:3050-3057 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | A chiral benzylic ether serves as an auxiliary for oxindole carboxylation (dr 5.2:1.0) that sets C10 configuration in a potential diazonamide precursor. The chiral substituent allows diastereomer separation and departs during a subsequent acid-catalyzed ring closure to form a tetracyclic aminal. With suitable N-protection, crystallization affords the aminal with 98-99% ee. |
| Databáze: | OpenAIRE |
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