scholarly journals Efficient Synthesis of the Insect Elicitor Volicitin and Biologically Active Analogs

2007 ◽  
Vol 2 (10) ◽  
pp. 1934578X0700201
Author(s):  
Venkat Krishnamachari ◽  
Xitao Xie ◽  
Shifang Zhu ◽  
Han-Xun Wei ◽  
Paul W Paré

An improved and efficient copper (I) mediated coupling procedure was used to synthesize N-(17-hydroxylinolenoyl)-L-glutamine (volicitin), a chemical elicitor from the herbivore pest beet army worm, and its biologically active analogs.

2004 ◽  
Vol 10 (3) ◽  
pp. 563-563
Author(s):  
Kamal Kumar ◽  
Dirk Michalik ◽  
Ivette Garcia Castro ◽  
Annegret Tillack ◽  
Alexander Zapf ◽  
...  

ChemInform ◽  
2010 ◽  
Vol 30 (39) ◽  
pp. no-no
Author(s):  
I. Moreno ◽  
I. Tellitu ◽  
R. SanMartin ◽  
D. Badia ◽  
L. Carrillo ◽  
...  

2004 ◽  
Vol 10 (3) ◽  
pp. 746-757 ◽  
Author(s):  
Kamal Kumar ◽  
Dirk Michalik ◽  
Ivette Garcia Castro ◽  
Annegret Tillack ◽  
Alexander Zapf ◽  
...  

2021 ◽  
Author(s):  
David Konrad ◽  
Peter Ruehmann ◽  
Hiroyasu Ando ◽  
Belinda Hetzler ◽  
Bryan Matsuura ◽  
...  

Tetrodotoxin (TTX) is an indispensable probe in neuroscience, a biosynthetic and ecological enigma, and one of the most celebrated targets of synthetic chemistry. Here, we present a stereoselective synthesis of TTX that proceeds in 22 steps starting from a readily available glucose derivative. The central cyclohexane ring of TTX and its α-tertiary amine moiety was established via the intramolecular 1,3-dipolar cycloaddition of a nitrile oxide, followed by alkynyl addition to the resultant isoxazoline. After some carefully chosen protecting group manipulations, a ruthenium-catalyzed hydroxylactonization set the stage for the formation of its dioxa-adamantane core. Installation of the guanidine, oxidation of a primary alcohol, and late-stage epimerization of the resultant aldehyde gave a mixture of TTX and anhydro TTX. Our synthesis represents one of the most effective of TTX reported to date and could give ready access to biologically active derivatives.


1988 ◽  
Vol 23 (3) ◽  
pp. 229-233
Author(s):  
J. A. Joyce ◽  
R. J. Ottens ◽  
G. A. Herzog ◽  
M. H. Bass

Laboratory cultures of field-collected larval tobacco budworm, Heliothis virescens (F.), beet army worm, Spodoptera exigua (Hübner), and fall armyworm, S. frugiperda (J. E. Smith) were bioassayed for response to three pyrethroids in combination with piperonyl butoxide (PBO), or MGK-264. The greatest synergistic effects were seen in S. exigua which also displayed the greatest tolerance to pyrethroids without synergists. The highest SR50 (synergist ratio) value for S. exigua was 22.1 with fenvalerate-PBO mixed in a ratio of 1:5, the highest for S. frugiperda was 4.6 with fenvalerate-MGK-264 1:5, and the highest for H. virescens was 1.3 with permethrin-MGK-264 1:5 or with fenvalerate-PBO 1:5.


2018 ◽  
Vol 42 (8) ◽  
pp. 6433-6440 ◽  
Author(s):  
Bapurao D. Rupanwar ◽  
Santosh S. Chavan ◽  
Anil M. Shelke ◽  
Gurunath M. Suryavanshi

A TfOH-catalyzed highly efficient synthesis of biologically active (E)-2-cyanoacrylamides and 3-substituted azetidine-2,4-diones has been reported with 64–94% yields under metal-free conditions.


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