13509-34-7Relevant articles and documents
Short Total Synthesis of [15N5]-Cylindrospermopsins from 15NH4Cl Enables Precise Quantification of Freshwater Cyanobacterial Contamination
Mailyan, Artur K.,Chen, Joanna L.,Li, Weiwei,Keller, Arturo A.,Sternisha, Shawn M.,Miller, Brian G.,Zakarian, Armen
supporting information, p. 6027 - 6032 (2018/05/05)
Fresh water cyanobacterial algal blooms represent a major health risk because these organisms produce cylindrospermopsin, a toxic, structurally complex, zwitterionic uracil-guanidine alkaloid recognized by the EPA as a dangerous drinking water contaminant. At present, the ability to detect and quantify the presence of cylindrospermospin in water samples is severely hampered by the lack of an isotopically labeled standard for analytical mass spectrometry. Herein, we present a concise, scaled total synthesis of 15N cylindrospermosin from 15N ammonium chloride, which leverages a unique stereoselective intramolecular double conjugate addition step to assemble the tricyclic guanidine core. In addition to providing the first pure isotopically labeled probe for precise quantification of this potent biotoxin in fresh water sources, our results demonstrate how unique constraints associated with isotope incorporation compel novel solutions to synthesis design.
An Unconventional Mechanistic Insight into SCF3 Formation from Difluorocarbene: Preparation of 18F-Labeled α-SCF3 Carbonyl Compounds
Zheng, Jian,Cheng, Ran,Lin, Jin-Hong,Yu, Dong-Hai,Ma, Longle,Jia, Lina,Zhang, Lan,Wang, Lu,Xiao, Ji-Chang,Liang, Steven H.
, p. 3196 - 3200 (2017/03/17)
Trifluoromethylthiolation by sulfuration of difluorocarbene with elemental sulfur is described for the first time, which overrides long-standing trifluoromethyl anion-based theory. Mechanistic elucidation reveals an unprecedented chemical process for the
Synthesis of isothiocyanates by reaction of amines with phenyl chlorothionoformate via one-pot or two-step process
Li, Zheng-Yi,Ma, Hong-Zhao,Han, Chen,Xi, Hai-Tao,Meng, Qi,Chen, Xin,Sun, Xiao-Qiang
, p. 1667 - 1674 (2013/07/19)
A facile and efficient synthesis of isothiocyanates from amines is described. This method involves the reaction of amines with phenyl chlorothionoformate in the presence of solid sodium hydroxide by either a one-pot process or a two-step approach. The one-pot process is useful for preparing alkyl and electron-rich aryl isothiocyanates, whereas the two-step approach is more versatile, working very well not only for alkyl and electron-rich aryl isothiocyanates, but also for highly electron-deficient aryl and heterocyclic isothiocyanates. Georg Thieme Verlag Stuttgart, New York.