927-73-1Relevant articles and documents
Scalable Total Synthesis, IP3R Inhibitory Activity of Desmethylxestospongin B, and Effect on Mitochondrial Function and Cancer Cell Survival
Podunavac, Ma?a,Mailyan, Artur K.,Jackson, Jeffrey J.,Lovy, Alenka,Farias, Paula,Huerta, Hernan,Molgó, Jordi,Cardenas, Cesar,Zakarian, Armen
supporting information, p. 11278 - 11282 (2021/04/19)
The scalable synthesis of the oxaquinolizidine marine natural product desmethylxestospongin B is based on the early application of Ireland–Claisen rearrangement, macrolactamization, and a late-stage installation of the oxaquinolizidine units by lactam reduction. The synthesis serves as the source of material to investigate calcium signaling and its effect on mitochondrial metabolism in various cell types, including cancer cells.
Total synthesis of carolacton, a highly potent biofilm inhibitor
Schmidt, Thomas,Kirschning, Andreas
supporting information; experimental part, p. 1063 - 1066 (2012/03/11)
Metals are the key players in the synthesis of caralacton, a strong inhibitor of bacterial biofilms. The total synthesis is based on several metal-mediated key transformations such as the Ley and the Duthaler-Hafner aldol reactions, the Marshall reaction and Breit's substitution, as well as the Nozaki-Hiyama-Kishi and Negishi-Fu C-C coupling reactions. Copyright
Rearrangement, nucleophilic substitution, and halogen switch reactions of alkyl halides over NaY zeolite: Formation of the bicyclobutonium cation inside the zeolite cavity
Franco, Marcelo,Rosenbach Jr., Nilton,Ferreira, Glaucio B.,Guerra, Antonio C. O.,Kover, W. Bruce,Turci, Cassia C.,Mota, Claudio J. A.
, p. 1592 - 1600 (2008/09/18)
Rearrangement and nucleophilic substitution of cyclopropylcarbinyl bromide over NaY and NaY impregnated with NaCl was observed at room temperature. The first-order kinetics are consistent with ionization to the bicyclobutonium cation, followed by internal return of the bromide anion or nucleophilic attack by impregnated NaCl to form cyclopropylcarbinyl, cyclobutyl, and allylcarbinyl chlorides. The product distribution analysis revealed that neither a purely kinetic distribution, similar to what is found in solution, nor the thermodynamic ratio, which favors the allylcarbinyl halide, was observed. Calculations showed that bicyclobutonium and cyclopropylcarbinyl carbocations are minimal over the zeolite structure, and stabilized by hydrogen bonding with the framework structure. A new process of nucleophilic substitution is reported, namely halogen switch, involving alkyl chlorides and bromides of different structures. The reaction occurs inside the zeolite pores, due to the confinement effects and is an additional proof of carbocation formation on zeolites. The results support the idea that zeolites act as solid solvents, permitting ionization and solvation of ionic species.
