scholarly journals Total synthesis of indole-3-acetonitrile-4-methoxy-2-C-β-d-glucopyranoside. Proposal for structural revision of the natural product

2012 ◽  
Vol 10 (27) ◽  
pp. 5194 ◽  
Author(s):  
Akop Yepremyan ◽  
Thomas G. Minehan
2015 ◽  
Vol 51 (28) ◽  
pp. 6202-6205 ◽  
Author(s):  
Matthew B. Calvert ◽  
Jonathan Sperry

A bioinspired synthetic approach to nominal yuremamine has uncovered the true structure of the natural product to be a flavonoidal indole.


2018 ◽  
Vol 16 (27) ◽  
pp. 5043-5049 ◽  
Author(s):  
Yi Man ◽  
Shaomin Fu ◽  
Juan Chen ◽  
Bo Liu

Asymmetric total synthesis of compound 1, as a proposed molecular structure of a natural product, in 11 steps is described. The inconsistency of the characterization data prompted us to propose a different structure as compound 2 and accordingly accomplish total synthesis in 9 steps and confirm the structural revision of this natural product.


2019 ◽  
Author(s):  
Moritz Honig ◽  
Erick Carreira

The first total synthesis of nominal harziane diterpenoid is disclosed, whose spectral characteristics did not match those of the reported natural product. Stereochemical analysis and subsequent synthesis of the epimeric tertiary alcohol led to reassignment of configuration of the natural product. At the heart of the synthesis is an enyne cycloisomerization that sets a key quaternary stereocenter within a cyclobutane with high diastereocontrol. The route features strategies for the synthesis of the highly congested 6–5–7–4 carbon skeleton characteristic of the caged harziane diterpenoids.


2019 ◽  
Author(s):  
Moritz Honig ◽  
Erick Carreira

The first total synthesis of nominal harziane diterpenoid is disclosed, whose spectral characteristics did not match those of the reported natural product. Stereochemical analysis and subsequent synthesis of the epimeric tertiary alcohol led to reassignment of configuration of the natural product. At the heart of the synthesis is an enyne cycloisomerization that sets a key quaternary stereocenter within a cyclobutane with high diastereocontrol. The route features strategies for the synthesis of the highly congested 6–5–7–4 carbon skeleton characteristic of the caged harziane diterpenoids.


2015 ◽  
Vol 17 (7) ◽  
pp. 1652-1655 ◽  
Author(s):  
B. Seetharamsingh ◽  
P. R. Rajamohanan ◽  
D. Srinivasa Reddy

ChemInform ◽  
2015 ◽  
Vol 46 (34) ◽  
pp. no-no
Author(s):  
B. Seetharamsingh ◽  
P. R. Rajamohanan ◽  
D. Srinivasa Reddy

2018 ◽  
Vol 16 (47) ◽  
pp. 9138-9142 ◽  
Author(s):  
Gorakhnath R. Jachak ◽  
Paresh R. Athawale ◽  
Heena Agarwal ◽  
Manoj Kumar Barthwal ◽  
Gianluigi Lauro ◽  
...  

Herein, we report the total synthesis of solomonamide A along with its structural revision for the first time.


Author(s):  
Ardalan A. Nabi ◽  
Lydia M. Scott ◽  
Daniel P. Furkert ◽  
Jonathan Sperry

The rare benzoxazepine ring in the alkaloid inducamide C is unstable and prone to rearrangement, indicating that structural revision of the natural product may be necessary.


Planta Medica ◽  
2013 ◽  
Vol 79 (10) ◽  
Author(s):  
M Albadry ◽  
Y Zou ◽  
Y Takahashi ◽  
A Waters ◽  
M Hossein ◽  
...  

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