390377-29-4Relevant academic research and scientific papers
A silver-promoted solid-phase guanidylation process enables the first total synthesis of stictamide A
Li, Xiang,Li, Yu-Lei,Chen, Yan,Zou, Yan,Zhuo, Xiao-Bin,Wu, Qiu-Ye,Zhao, Qing-Jie,Hu, Hong-Gang
, p. 94654 - 94657 (2015/11/24)
The first total synthesis of stictamide A, a structurally unique peptide with a statine motif and a N-prenyl modified arginine in the side chain, is disclosed. The requisite statine was achieved via stereoselective hydrogenation of a functionalized ketone. The N-prenyl modified arginine was constructed by a novel silver-promoted solid-phase strategy for the first time. This synthetic method can be generally applied to the efficient synthesis of peptides containing statine and/or arginine N-alkylation groups.
Total synthesis and stereochemical reassignment of tasiamide B
Sun, Tiantian,Zhang, Wei,Zong, Chengli,Wang, Peng,Li, Yingxi
experimental part, p. 364 - 374 (2011/03/22)
The first total synthesis of tasiamide B, an octapeptide bearing 4-amino-3-hydroxy-5-phenylpentanoic acid unit isolated from the marine cyanobacteria Symploca sp. is described. A simple and efficient way was found to avoid the pyroglutamylation of Nα-Me-Gln and led to a reassignment of the Nα-Me-L-Phe of tasiamide B to be N α-Me-D-Phe, which was also supported by 1D and 2D NMR. Copyright
Diastereoselective synthesis of enantiopure γ-amino-β-hydroxy acids by Reformatsky reaction of chiral α-dibenzylamino aldehydes
Andrés, José M,Pedrosa, Rafael,Pérez, Alberto,Pérez-Encabo, Alfonso
, p. 8521 - 8530 (2007/10/03)
N,N-Dibenzylamino aldehydes 1 react with Reformatsky's reagent leading to anti-γ-dibenzylamino-β-hydroxy esters 2 as the major stereoisomers. Treatment of 2 with TFA followed by hydrogenolysis on Pearlman's catalyst yields the corresponding γ-amino-β-hydroxy acids 10. Contrarily, some N-butoxycarbonyl (Boc) amino aldehydes lead to syn-γ-tert-butoxycarbonylamino-β-hydroxy esters as the major product.
