Anion-Accelerated Aromatic Oxy-Cope Rearrangement in Geranylation/Nerylation of Xanthone: Stereochemical Insights and Synthesis of Fuscaxanthone F

Synlett ◽  
2020 ◽  
Vol 31 (14) ◽  
pp. 1378-1383
Author(s):  
Takashi Matsumoto ◽  
Yuuki Fujimoto ◽  
Kanae Takahashi ◽  
Ryouma Kobayashi ◽  
Haruhiko Fukaya ◽  
...  
Keyword(s):  
Transition State ◽  
Side Chain ◽  
Cope Rearrangement ◽  
State Structure ◽  
Transition State Structure

An efficient installation of a 3,7-dimethylocta-2,6-dien-1-yl (geranyl or neryl) side chain at the C(1) position of a xanthone core by utilizing an anion-accelerated aromatic oxy-Cope rearrangement is described. Experiments revealed that this uncommon rearrangement takes place in a stereospecific manner through a chair-like transition-state structure. An application to the syntheses of the natural xanthone fuscaxanthone F, possessing a geranyl side chain, and its neryl analogue is also described.

Rearrangement of chorismate to prephenate. Use of chorismate mutase inhibitors to define the transition state structure

Biochemistry ◽  
1977 ◽  
Vol 16 (22) ◽  
pp. 4848-4852 ◽  
Author(s):  
P. R. Andrews ◽  
E. N. Cain ◽  
E. Rizzardo ◽  
G. D. Smith
Keyword(s):  
Transition State ◽  
Chorismate Mutase ◽  
State Structure ◽  
Transition State Structure

Conservation of Transition State Structure in Fast Folding Peripheral Subunit-Binding Domains

2008 ◽  
Vol 383 (1) ◽  
pp. 224-237 ◽  
Author(s):  
Timothy D. Sharpe ◽  
Neil Ferguson ◽  
Christopher M. Johnson ◽  
Alan R. Fersht
Keyword(s):  
Transition State ◽  
State Structure ◽  
Transition State Structure ◽  
Binding Domains
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