1286738-59-7Relevant academic research and scientific papers
Total synthesis and biological evaluation of spirotryprostatin A analogs
Ma, Yangmin,Fan, Chao,Jia, Bin,Cheng, Pei,Liu, Jia,Ma, Yuqiang,Qiao, Ke
, p. 737 - 746 (2017/10/17)
Based on the spirotryprostatin A structure, a series of compounds belonging to spiro-indolyl diketopiperazine structural class were designed and synthesized, which embody an oxindole with an all-carbon quaternary stereocenter. The total synthesis can efficiently be accessed in a seven-step reaction sequence with 18–28% overall yield from commercially available materials, and a highly enantioselective 1,3-dipolar cycloaddition, N-acylation of the resulting stereochemically complex spiro[pyrrolidin-3,3′-oxindole]s core with Fmoc-L-pro-Cl and spontaneous ring closure upon N-deprotection were obtained. The synthesized compounds 13a–e and 15a–e were evaluated for their antibacterial activities. The result showed that compounds 13b and 15b were active only against Gram-positive bacteria, and selective antibacterial activity was exhibited by compounds 13d and 13e against Streptococcus lactis. Further, all the remaining compounds showed a certain degree of antibacterial activity. In addition, the structure–activity relationship is also discussed.
Catalytic asymmetric 1,3-dipolar cycloaddition of N-unprotected 2-oxoindolin-3-ylidene derivatives and azomethine ylides for the construction of spirooxindole-pyrrolidines
Liu, Tang-Lin,Xue, Zhi-Yong,Tao, Hai-Yan,Wang, Chun-Jiang
experimental part, p. 1980 - 1986 (2011/04/25)
Asymmetric 1,3-dipolar cycloaddition of N-unprotected 2-oxoindolin-3- ylidene with azomethine ylides for the construction of spirooxindole- pyrrolidines bearing four contiguous stereogenic centers has been achieved with AgOAc/TF-BiphamPhos complexes for t
