1286738-58-6Relevant 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.
The copper-catalyzed asymmetric construction of a dispiropyrrolidine skeleton via 1,3-dipolar cycloaddition of azomethine ylides to α-alkylidene succinimides
Yang, Wu-Lin,Liu, Yang-Zi,Luo, Shuai,Yu, Xingxin,Fossey, John S.,Deng, Wei-Ping
supporting information, p. 9212 - 9215 (2015/06/08)
A highly efficient asymmetric 1,3-dipolar cycloaddition of azomethine ylides to α-alkylidene succinimides catalyzed by a novel chiral N,O-ligand/Cu(OAc)2 system is reported, affording dispiropyrrolidine derivatives with spiro quaternary stereog
PyBidine-Cu(OTf)2-catalyzed asymmetric [3+2] cycloaddition with imino esters: Harmony of Cu-lewis acid and imidazolidine-NH hydrogen bonding in concerto catalysis
Arai, Takayoshi,Ogawa, Hiroki,Awata, Atsuko,Sato, Makoto,Watabe, Megumi,Yamanaka, Masahiro
supporting information, p. 1595 - 1599 (2015/01/30)
A bis(imidazolidine)pyridine (PyBidine)-Cu(OTf)2 complex catalyzing the endo-selective [3+2] cycloaddition of nitroalkenes with imino esters was applied to the reaction of methyleneindolinones with imino esters to afford spiro[pyrrolidin-3, 3′-
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
