Enantioselective Total Syntheses of (+)-Fendleridine and (+)-Acetylaspidoalbidine
| Autor: | Luke A. Kassekert, Arun K. Ghosh, Joshua R. Born |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
010405 organic chemistry
Stereochemistry Extramural Fendleridine Organic Chemistry Intramolecular cyclization Enantioselective synthesis Ether Stereoisomerism Chemistry Techniques Synthetic 010402 general chemistry 01 natural sciences Article 0104 chemical sciences Indole Alkaloids chemistry.chemical_compound chemistry |
| Zdroj: | J Org Chem |
| ISSN: | 1520-6904 |
| Popis: | Enantioselective syntheses of hexacyclic aspidoalbidine alkaloids (+)-fendleridine (2) and (+)-acetylaspidoalbidine (3) are described. These syntheses feature an asymmetric decarboxylative allylation and photocyclization of a highly substituted enaminone. Also, the synthesis highlights the formation of the C19 hemiaminal ether via a reduction/condensation/intramolecular cyclization cascade with the C21-alcohol. The present synthesis provides convenient access to the aspidoalbidine hexacyclic alkaloid family in an efficient manner. |
| Databáze: | OpenAIRE |
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