A Short Access to the Skeleton of Elisabethin A and Formal Syntheses of Elisapterosin B and Colombiasin A
| Autor: | Johann Mulzer, Johannes Preindl, Christian Leitner, Simon Baldauf |
|---|---|
| Rok vydání: | 2014 |
| Předmět: |
Bridged-Ring Compounds
chemistry.chemical_classification Annulation Ketone Molecular Structure Sulfonium Stereochemistry Organic Chemistry Stereoisomerism Ring (chemistry) Biochemistry Combinatorial chemistry Aldehyde chemistry.chemical_compound chemistry Decalin Ylide Diterpenes Physical and Theoretical Chemistry Ene reaction |
| Zdroj: | Organic Letters. 16:4276-4279 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol501998y |
| Popis: | A short stereoselective synthesis of the Elisabethin A skeleton 4 is described, which opens a formal access to the diterpenes Elisapterosin B and Colombiasin A as well. Key reactions were an intermolecular endo-selective Diels-Alder reaction to generate the decalin part of the molecule, a chemo- and diastereoselective allylation of an aldehyde with allylzinc, a palladium ene annulation of the cyclopentane ring, and a novel sulfonium ylide induced fragmentation of a polycyclic ketone. Additional insights have been gained for the crucial epimerization at C-2. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|