| Autor: |
Julia Becker, Martin Hiersemann, Valeska von Kiedrowski, Florian Quentin, Lena Butt, Elisabeth Mischler |
| Rok vydání: |
2014 |
| Předmět: |
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| Zdroj: |
The Journal of organic chemistry. 79(7) |
| ISSN: |
1520-6904 |
| Popis: |
The enantioselective synthesis of (−)-9,10-dihydroecklonialactone B is described. The catalytic asymmetric Claisen rearrangement of a Gosteli-type allyl vinyl ether was utilized to afford an acyclic α-keto ester building block endowed with functionality amenable to the preparation of the carbocyclic target molecule by suitable postrearrangement transformations: A highly diastereoselective Corey–Bakshi–Shibata reduction of a β-chiral α-keto ester and a reductive homologation of an α-hydroxy ester. A transprotection tactic by a chemoselective intramolecular 6-exo-trig iodoetherification enabled regioselective ring-closing alkene metatheses to afford the 5- as well as the 14-membered ring, however, with mixed success in terms of E/Z selectivity. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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