Stereoselective Total Synthesis of (+)-Streptazolin by Using a Temporary Silicon-Tethered RCM Strategy
| Autor: | Fangzheng Li, Marvin J. Miller |
|---|---|
| Rok vydání: | 2006 |
| Předmět: |
Silicon
Intramolecular reaction Stereochemistry Organic Chemistry Molecular Conformation Total synthesis Stereoisomerism Cyclopentanes Metathesis Chemical synthesis chemistry.chemical_compound Piperidines chemistry Cyclization Intramolecular force Aldol condensation Piperidine Oxidation-Reduction Streptazolin |
| Zdroj: | The Journal of Organic Chemistry. 71:5221-5227 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo060555y |
| Popis: | A stereoselective total synthesis of (+)-streptazolin 1 was accomplished starting from readily available aminocyclopentenol (-)-7. The synthetic sequence highlights an intramolecular aldol condensation strategy to construct the piperidine core and a silicon-tethered ring-closing metathesis strategy to install the Z exocyclic ethylidene side chain of streptazolin. Separate protodesilylation and Tamao oxidation of a common intermediate 32 afforded streptazolin and the precursor for 13-hydroxystreptazolin. The overall yield for (+)-streptazolin 1 from aminocyclopentenol (-)-7 was 4.8% for a total of 16 steps. |
| Databáze: | OpenAIRE |
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