Asymmetric Synthesis of the Tricyclooctane Core of Trachylobane Natural Products and Related Terpenoids
| Autor: | Michael Schneider, Erick M. Carreira, Simon Krautwald, Matthieu J. R. Richter |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Biological Products Ketone 010405 organic chemistry Cyclopropanation Terpenes Organic Chemistry Enantioselective synthesis Alcohol 010402 general chemistry Octanes 01 natural sciences Biochemistry Terpenoid Cycloaddition 0104 chemical sciences chemistry.chemical_compound chemistry Yield (chemistry) Organic chemistry Physical and Theoretical Chemistry |
| Zdroj: | Organic letters. 21(21) |
| ISSN: | 1523-7052 |
| Popis: | Enantioselective synthesis of a highly versatile building block en route to trachylobanes and related terpenoids is presented. The synthesis features diastereoselective Diels-Alder cycloaddition reaction, a cyclopropanation/homoquadricyclane rearrangement cascade, and palladium-catalyzed C-H acetoxylation. The targeted tricyclooctane was obtained in 20% yield over 8 steps and in 95% ee. The ketone and alcohol functional groups serve as handles for further elaboration. |
| Databáze: | OpenAIRE |
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