62596-65-0Relevant academic research and scientific papers
Synthesis of tubuvaline (Tuv) fragment of tubulysin via diastereoselective dihydroxylation of homoallylamine
Reddy, Ramesh B.,M, Vijay,Krishnan, Mena Asha,Chelvam, Venkatesh
supporting information, p. 797 - 809 (2020/12/13)
Tubulysins are natural anticancer molecules that directly bind and inhibit tubulin polymerization in actively dividing cells leading to apoptosis and cell death. Structurally, tubulysins are linear tetrapeptides, constituted by a natural amino acid (Ile)
Synthesis and hetero-Diels-Alder reactions of enantiomerically pure dihydro-1: H -azepines
Craig, Donald,Spreadbury, Samuel R. J.,White, Andrew J. P.
supporting information, p. 9803 - 9806 (2020/09/16)
Thermolysis of enantiomerically pure 3-substituted 7,7-dihalo-2-azabicyclo[4.1.0]heptanes in the presence of K2CO3 gives in good yields 2-alkyl-6-halo-1-tosyl-2,3-dihydro-1H-azepines. These undergo highly stereoselective [4+2] cycloaddition reactions with heterodienophiles and arylation/alkenylation under Suzuki conditions.
Synthesis of the Deacetoxytubuvaline Fragment of Pretubulysin and its Lipophilic Analogues for Enhanced Permeability in Cancer Cell Lines
Reddy, Ramesh B.,Dudhe, Premansh,Chelvam, Venkatesh
supporting information, p. 77 - 81 (2019/01/04)
In the last two decades, tubulysins have emerged as alternatives to microtubule depolymerizing agents such as colchicine and vinblastine, which are well-established anticancer agents. However, the complex structure of tubulysins has always posed a challen
Cu-Catalyzed [3 + 3] Cycloaddition of Isocyanoacetates with Aziridines and Stereoselective Access to α,γ-Diamino Acids
Kok, Germaine Pui Yann,Yang, Hui,Wong, Ming Wah,Zhao, Yu
supporting information, p. 5112 - 5115 (2018/09/12)
We report herein an efficient Cu-catalyzed formal [3 + 3] cycloaddition of isocyanoacetates with readily available aziridines of different substitution patterns, which provides a practical access to valuable 1,4,5,6-tetrahydropyrimidine derivatives. In pa
An efficient synthetic approach for N-C bond formation from (S)-amino acids: An easy access to cis-2,5-disubstituted chiral piperazines
Manna, Sudipta Kumar,Panda, Gautam
, p. 18332 - 18338 (2013/10/21)
An efficient synthetic strategy is described for the construction of amino acids derived enantiomerically pure cis-2,5-disubstituted chiral piperazines. Cu-catalyzed spontaneous regioselective ring opening and ring closing of non-activated N-tosyl aziridines as well as Pd-mediated N-C bond formation from N-tosyl halogenated amino-derivatives are the key steps for accessing disubstituted piperazines.
One-pot and microwave-assisted synthesis of N-sulfonylaziridines
Xu, Hao,Tian, Hua,Zheng, Liangyu,Liu, Qingwen,Wang, Li,Zhang, Suoqin
experimental part, p. 2873 - 2875 (2011/06/21)
A novel and efficient microwave-assisted one-step reaction was developed to synthesize chiral N-sulfonylaziridines by the reaction of different chiral amino alcohols and sulfonic chlorides. The newly developed microwave synthetic method has the advantage of reducing the reaction time from 24 to 0.5 h with improved yields (84-93%) and minimizing by-products.
Regioselective ring-opening of amino acid-derived chiral aziridines: An easy access to cis-2,5-disubstituted chiral piperazines
Samanta, Krishnananda,Panda, Gautam
supporting information; experimental part, p. 189 - 197 (2011/10/08)
An efficient four-step synthetic strategy for cis-2,5-disubstituted chiral piperazines derived from amino-acid-based aziridines is described. The key steps in this strategy are the highly regioselective boron trifluoride diethyl etherate (BF3·OEt2)-mediated ring-opening of less-reactive N-Ts chiral aziridines by α-amino acid methyl ester hydrochloride followed by Mitsunobu cyclization. This protocol has been used in an attempt to construct the piperazine core framework of natural product (+)-piperazinomycin. The pied piperazines: A four-step efficient synthetic strategy for cis-2,5-disubstituted chiral piperazines derived from amino acid-based aziridines is described. The key reaction steps are the highly regioselective BF3·OEt2 mediated ring-opening of less-reactive N-Ts chiral aziridines by α-amino acid methyl ester hydrochlorides, followed by a Mitsunobu cyclization. This protocol has been used in an attempt to construct the piperazine core framework of natural product (+)-piperazinomycin. Copyright
Enantioselective copper-catalyzed 1,4-addition of dialkylzincs to enones followed by trapping with allyl iodide derivatives
Kawamura, Kenjiro,Fukuzawa, Hitomi,Hayashi, Masahiko
scheme or table, p. 640 - 647 (2011/08/06)
Enantioselective copper-catalyzed 1,4-addition of dialkylzincs to enones proceeded in the presence of 0.1 mol% of Cu(OTf)2 and 0.25 mol% of an N,N,P-ligand containing a quinoline moiety to afford the corresponding conjugated adducts in 99%ee. The intermediate zinc enolates were trapped with substituted allyl iodides to give disubstituted ketones with high diastereoselectivity and enantioselectivity.
Enantioselective intramolecular Rauhut-Currier reaction catalyzed by chiral phosphinothiourea
Gong, Jing-Jing,Li, Tian-Ze,Pan, Kun,Wu, Xin-Yan
supporting information; experimental part, p. 1491 - 1493 (2011/03/22)
Chiral organophosphine-catalyzed enantioselective Rauhut-Currier reaction has been disclosed for the first time. With l-valine-derived phosphinothiourea, the intramolecular Rauhut-Currier reaction of bis(enones) was achieved in good yields (up to 99%) wit
Synthesis and biological evaluation of reversible inhibitors of IdeS, a bacterial cysteine protease and virulence determinant
Berggren, Kristina,Johansson, Bjoern,Fex, Tomas,Kihlberg, Jan,Bjoerck, Lars,Luthman, Kristina
scheme or table, p. 3463 - 3470 (2009/09/25)
Analogues of the irreversible protease inhibitors TPCK and TLCK have been synthesized and tested as inhibitors of the bacterial cysteine protease IdeS excreted by Streptococcus pyogenes. Eight compounds were identified as inhibitors of IdeS in an in vitro
