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 |
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Keywords
- dearomatization
- hydrogenation
- natural products
- terpenoids
- total synthesis
ASJC Scopus subject areas
- Chemistry(all)
- Catalysis
Cite this
Total synthesis of vinigrol. / Yang, Qingliang; Njardarson, Jon T; Draghici, Cristian; Li, Fang.
In: Angewandte Chemie - International Edition, Vol. 52, No. 33, 12.08.2013, p. 8648-8651.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Total synthesis of vinigrol
AU - Yang, Qingliang
AU - Njardarson, Jon T
AU - Draghici, Cristian
AU - Li, Fang
PY - 2013/8/12
Y1 - 2013/8/12
N2 - 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.
AB - 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.
KW - dearomatization
KW - hydrogenation
KW - natural products
KW - terpenoids
KW - total synthesis
UR - http://www.scopus.com/inward/record.url?scp=84882337111&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84882337111&partnerID=8YFLogxK
U2 - 10.1002/anie.201304624
DO - 10.1002/anie.201304624
M3 - Article
VL - 52
SP - 8648
EP - 8651
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 33
ER -