A Convergent Synthesis of the Cardenolide Skeleton: Intramolecular Aldol Condensation via Reduction of α-Bromoketones
| Autor: | Daniel Chapdelaine, Julie Belzile, Pierre Deslongchamps |
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| Rok vydání: | 2002 |
| Předmět: |
Models
Molecular Intramolecular reaction Stereochemistry Organic Chemistry Molecular Conformation Convergent synthesis Total synthesis Ketones Condensation reaction Chemical synthesis Cardenolides Structure-Activity Relationship chemistry.chemical_compound chemistry Cyclohexenone Cardenolide Steroids Aldol condensation Oxidation-Reduction |
| Zdroj: | The Journal of Organic Chemistry. 67:5669-5672 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo025612b |
| Popis: | Synthesis of the highly biologically valuable cardenolide backbone was achieved via anionic polycyclization. Bromoketone 18, obtained from double-Michael cycloaddition between cyclohexenone 14 and gamma,delta-unsaturated beta-ketoester 16, was efficiently aldolized under reductive conditions. The highly functionalized tetracyclic compound 52 is an important synthetic intermediate that is potentially amenable to natural cardenolide total synthesis. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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