1010127-36-2Relevant academic research and scientific papers
Catalytic δ-hydroxyalkynone rearrangement in the stereoselective total synthesis of centrolobine, engelheptanoxides A and C and analogues
Ahmad, Mohammad N.,Chopra, Sidharth,Fernandes, Rodney A.,Kumar, Praveen
, (2021/08/13)
A catalytic stereoselective total synthesis of centrolobine and engelheptanoxides A and C has been completed via a metal-free catalytic δ-hydroxyalkynone rearrangement to 2,3-dihydro-4H-pyran-4-one and diastereoselective hydrogenation to the all syn-2,4,6-trisubstituted pyran strategy. The onliest required chirality was introduced by Jacobsen kinetic resolution, which further directed the diastereoselective hydrogenation. A first stereoselective synthesis of engelheptanoxide A is also accomplished. The analogues and derivatives of centrolobine and engelheptanoxides prepared were evaluated for antitubercular activity against M. tuberculosis H37Rv ATCC 27294.
Design, synthesis, and evaluation of curcumin-derived arylheptanoids for glioblastoma and neuroblastoma cytotoxicity
Campos, Catherine A.,Gianino, Joseph B.,Bailey, Barbara J.,Baluyut, Mary E.,Wiek, Constanze,Hanenberg, Helmut,Shannon, Harlan E.,Pollok, Karen E.,Ashfeld, Brandon L.
supporting information, p. 6874 - 6878 (2014/01/06)
Using an innovative approach toward multiple carbon-carbon bond-formations that relies on the multifaceted catalytic properties of titanocene complexes we constructed a series of C1-C7 analogs of curcumin for evaluation as brain and peripheral nervous system anti-cancer agents. C2-Arylated analogs proved efficacious against neuroblastoma (SK-N-SH & SK-N-FI) and glioblastoma multiforme (U87MG) cell lines. Similar inhibitory activity was also evident in p53 knockdown U87MG GBM cells. Furthermore, lead compounds showed limited growth inhibition in vitro against normal primary human CD34+hematopoietic progenitor cells. Taken together, the present findings indicate that these curcumin analogs are viable lead compounds for the development of new central and peripheral nervous system cancer chemotherapeutics with the potential for little effects on normal hematopoietic progenitor cells.
Titanocene-catalyzed multicomponent coupling approach to diarylethynyl methanes
Gianino, Joseph B.,Ashfeld, Brandon L.
supporting information, p. 18217 - 18220,4 (2012/12/12)
A titanocene-catalyzed multicomponent coupling to provide diarylethynyl methanes is described. By combining the multifunctionality of Cp 2TiCl2 with the traceless dielectrophilicity of aryl aldehydes, all-carbon tertiary centers are obtained in 55-99% yield.
Titanocene-catalyzed multicomponent coupling approach to diarylethynyl methanes
Gianino, Joseph B.,Ashfeld, Brandon L.
supporting information, p. 18217 - 18220 (2013/01/15)
A titanocene-catalyzed multicomponent coupling to provide diarylethynyl methanes is described. By combining the multifunctionality of Cp 2TiCl2 with the traceless dielectrophilicity of aryl aldehydes, all-carbon tertiary centers are obtained in 55-99% yield.
An efficient approach to the stereoselective synthesis of 2,6-disubstituted dihydropyrans via stannyl-Prins cyclization
Dziedzic, Magdalena,Furman, Bart?omiej
, p. 678 - 681 (2008/09/16)
A general method has been developed for the stereoselective construction of 2,6-disubstituted dihydropyrans based on the Lewis acid-catalyzed intramolecular reactions of oxocarbenium ions with vinylstannanes. This novel methodology was applied to the enan
