20425-54-1Relevant articles and documents
A short stereoselective total synthesis of the fusarium toxin equisetin.
Burke,Dixon,Ley,Rodriguez
, p. 3611 - 3613 (2000)
A short stereoselective synthesis of the fusarium toxin equisetin, an N-methylserine-derived acyl tetramic acid and potent inhibitor of HIV-1 integrase enzyme, is described using as the key step a stereoselective lithium perchlorate mediated intramolecular Diels-Alder reaction of a fully conjugated E,E,E-triene with a trisubstituted gamma,delta-unsaturated beta-ketothioester.
Total synthesis of the Fusarium toxin equisetin
Burke, Lisa T.,Dixon, Darren J.,Ley, Steven V.,Rodriguez, Felix
, p. 274 - 280 (2005)
A short stereoselective synthesis of the Fusarium toxin equisetin, a potent inhibitor of HIV-1 integrase enzyme is described, using as the key step a stereoselective intramolecular Diels-Alder reaction of a fully conjugated E,E,E-triene with a trisubstituted γ,δ-unsaturated β-ketothioester.
Relative stereochemical assignment of C-33 and C-35 in the antibiotic gladiolin
Perry, Christopher,Sargeant, Jacob R.,Song, Lijiang,Challis, Gregory L.
, p. 5150 - 5155 (2018)
Gladiolin is a macrolide antibiotic isolated from Burkholderia gladioli BCC0238 with promising activity against Mycobacterium tuberculosis, including several multidrug resistant strains. The configuration of all but one of the stereogenic centers of gladiolin has previously been elucidated using a combination of NOESY NMR experiments and predictive sequence analysis of the polyketide synthase responsible for its assembly. However, it was not possible to assign the configuration of the C-35 methyl group using such methods. Here we report the synthesis of C-33/C-35-syn and C-33/C-35-anti mimics of the C-30 to C-38 fragment of gladiolin from (R) and (S)-citronellol, respectively. Comparison of HSQC NMR data for the mimics and the natural product showed that the C-35 methyl is anti to the C-33 hydroxyl group, indicating that gladiolin has the 35S configuration.
Amide/Iminium Zwitterionic Catalysts for (Trans)esterification: Application in Biodiesel Synthesis
Lam, Ying-Pong,Ng, Wing-Hin,Tan, Fei,Tse, Ying-Lung Steve,Wang, Xinyan,Yeung, Ying-Yeung
, p. 8083 - 8092 (2019/08/26)
A class of zwitterionic organocatalysts based on an amide anion/iminium cation charge pair has been developed. The zwitterions are easily prepared by reacting aziridines with aminopyridines. They are catalytically applicable to transesterifications and dehydrative esterifications. Mechanistic studies reveal that the amide anion and iminium cation work synergistically in activating the reaction partners, with the iminium cationic moiety interacting with the carbonyl substrates through nonclassical hydrogen bonding. The reaction can be applied to large-scale synthesis of biodiesel under mild conditions.
One-pot sequence for reductive-acetylation of carbonyl compounds with (N-methylimidazole)(tetrahydroborato)zinc complex
Setamdideh, Davood,Khezri, Behrooz
experimental part, p. 5766 - 5772 (2012/07/28)
Reductive-acetylation of variety of aliphatic and aromatic aldehydes and ketones, α,β-unsaturated carbonyl compounds are examined efficiently with (N-methylimidazole)(tetrahydroborato)zinc complex, [Zn(BH4) 2(nmi)], under mild condition in THF at room temperature or reflux conditions. The corresponding acetates were obtained in excellent yields (90-98 %).
