Abstract
Carbocyclic cage fight: The substrate-controlled total synthesis of vinigrol features a strategic oxidative dearomatization/Diels-Alder cycloaddition reaction and a subsequent palladium-catalyzed cyclization cascade to construct the carbocyclic core. The C4, C9, and C12 stereocenters were installed using either reduction or oxidation reactions, and the diterpenoid core was unraveled by a ring fragmentation reaction.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 8648-8651 |
| Number of pages | 4 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 52 |
| Issue number | 33 |
| DOIs | |
| State | Published - Aug 12 2013 |
Keywords
- dearomatization
- hydrogenation
- natural products
- terpenoids
- total synthesis
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
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Cite this
Yang, Q., Njardarson, J. T., Draghici, C., & Li, F. (2013). Total synthesis of vinigrol. Angewandte Chemie - International Edition, 52(33), 8648-8651. https://doi.org/10.1002/anie.201304624