Extending Pummerer Reaction Chemistry: Application to the Assembly of the Pentacyclic Core of Dibromopalau’amine
| Autor: | Ken S. Feldman, Ahmed Yimam Nuriye |
|---|---|
| Rok vydání: | 2010 |
| Předmět: |
Models
Molecular Molecular Structure Stereochemistry Pummerer rearrangement Organic Chemistry Stereoisomerism Model system Wolff rearrangement Crystallography X-Ray Guanidines Biochemistry Bromine Compounds chemistry.chemical_compound chemistry Cyclization Spiro Compounds Amine gas treating Physical and Theoretical Chemistry Oxidation-Reduction Octane |
| Zdroj: | Organic Letters. 12:4532-4535 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | A pentacyclic model system featuring the trans azabicyclo[3.3.0]octane unit of dibromopalau'amine was prepared with complete diastereoselectivity in the polycyclic core from a tricyclic precursor. The key transformations of this sequence include (a) a Pummerer reaction-mediated oxidative bicyclization, and (b) a Wolff rearrangement-based ring contraction to deliver the strained azabicyclo[3.3.0]octane core. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|