scholarly journals Computational and Synthetic Investigation of Cationic Rearrangement in the Putative Biosynthesis of Justicane Triterpenoids

Author(s):  
Masha Elkin ◽  
Anthony Scruse ◽  
Aneta Turlik ◽  
Timothy Newhouse

<div> <div> <div> <p>A biomimetic cationic structural rearrangement of the oleanolic acid framework is reported for the gram-scale synthesis and structural reassignment of justicioside E aglycone. The mechanism of the putative biosynthetic rearrangement is investigated with kinetic, computational, and synthetic approaches. The precursor to rearrangement was accessed through two strategic advancements: (1) synthesis of a 1,3-diketone via oxidation of a β-silyl enone, and (2) diastereoselective 1,3-diketone reduction to form a syn-1,3-diol using SmI2 with PhSH as a key additive. </p> </div> </div> </div>

2018 ◽  
Author(s):  
Masha Elkin ◽  
Anthony Scruse ◽  
Aneta Turlik ◽  
Timothy Newhouse

<div> <div> <div> <p>A biomimetic cationic structural rearrangement of the oleanolic acid framework is reported for the gram-scale synthesis and structural reassignment of justicioside E aglycone. The mechanism of the putative biosynthetic rearrangement is investigated with kinetic, computational, and synthetic approaches. The precursor to rearrangement was accessed through two strategic advancements: (1) synthesis of a 1,3-diketone via oxidation of a β-silyl enone, and (2) diastereoselective 1,3-diketone reduction to form a syn-1,3-diol using SmI2 with PhSH as a key additive. </p> </div> </div> </div>


2018 ◽  
Author(s):  
Masha Elkin ◽  
Anthony Scruse ◽  
Aneta Turlik ◽  
Timothy Newhouse

<div> <div> <div> <p>A biomimetic cationic structural rearrangement of the oleanolic acid framework is reported for the gram-scale synthesis and structural reassignment of justicioside E aglycone. The mechanism of the putative biosynthetic rearrangement is investigated with kinetic, computational, and synthetic approaches. The precursor to rearrangement was accessed through two strategic advancements: (1) synthesis of a 1,3-diketone via oxidation of a β-silyl enone, and (2) diastereoselective 1,3-diketone reduction to form a syn-1,3-diol using SmI2 with PhSH as a key additive. </p> </div> </div> </div>


2018 ◽  
Vol 131 (4) ◽  
pp. 1037-1041 ◽  
Author(s):  
Masha Elkin ◽  
Anthony C. Scruse ◽  
Aneta Turlik ◽  
Timothy R. Newhouse

2019 ◽  
Vol 58 (4) ◽  
pp. 1025-1029 ◽  
Author(s):  
Masha Elkin ◽  
Anthony C. Scruse ◽  
Aneta Turlik ◽  
Timothy R. Newhouse

2020 ◽  
Vol 11 (48) ◽  
pp. 7603-7624
Author(s):  
Ismail Altinbasak ◽  
Mehmet Arslan ◽  
Rana Sanyal ◽  
Amitav Sanyal

This review provides an overview of synthetic approaches utilized to incorporate the thiol-reactive pyridyl-disulfide motif into various polymeric materials, and briefly highlights its utilization to obtain functional materials.


Planta Medica ◽  
2009 ◽  
Vol 75 (09) ◽  
Author(s):  
CM Strüh ◽  
S Jäger ◽  
CM Schempp ◽  
T Jakob ◽  
A Scheffler ◽  
...  

Planta Medica ◽  
2016 ◽  
Vol 81 (S 01) ◽  
pp. S1-S381
Author(s):  
K Mulsow ◽  
J Rolff ◽  
S Jaeger ◽  
MF Melzig

This review paper covers the major synthetic approaches attempted towards the synthesis of some Non-Steroidal Anti-Inflammatory Drugs (Naproxen, Ibuprofen and Nabumetone)


2020 ◽  
Author(s):  
Jennifer A. Rudd ◽  
Ewa Kazimierska ◽  
Louise B. Hamdy ◽  
Odin Bain ◽  
Sunyhik Ahn ◽  
...  

The utilization of carbon dioxide is a major incentive for the growing field of carbon capture. Carbon dioxide could be an abundant building block to generate higher value products. Herein, we describe the use of porous copper electrodes to catalyze the reduction of carbon dioxide into higher value products such as ethylene, ethanol and, notably, propanol. For <i>n</i>-propanol production, faradaic efficiencies reach 4.93% at -0.83 V <i>vs</i> RHE, with a geometric partial current density of -1.85 mA/cm<sup>2</sup>. We have documented the performance of the catalyst in both pristine and urea-modified foams pre- and post-electrolysis. Before electrolysis, the copper electrode consisted of a mixture of cuboctahedra and dendrites. After 35-minute electrolysis, the cuboctahedra and dendrites have undergone structural rearrangement. Changes in the interaction of urea with the catalyst surface have also been observed. These transformations were characterized <i>ex-situ</i> using scanning electron microscopy, X-ray diffraction, and X-ray photoelectron spectroscopy. We found that alterations in the morphology, crystallinity, and surface composition of the catalyst led to the deactivation of the copper foams.


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