493-05-0Relevant articles and documents
Target directed enediyne prodrugs: hER and AhR degradation by a synthetic oxo-enediyne
Jones, Graham B.,Kilgore, Michael W.,Pollenz, Richard S.,Li, Aiwen,Mathews, Jude E.,Wright, Justin M.,Huber, Robert S.,Tate, Patricia L.,Price, Thomas L.,Sticca, Robert P.
, p. 1971 - 1976 (1996)
An efficient route to oxo-enediynes is presented. A simple oxo-enediyne has been synthesized, which cyclizes to give an isochroman. The agent shows cytotoxicity for ER rich breast cancer cells and a model for its mode of action is proposed.
Iridium-Catalyzed Enantioselective Hydrogenation of Oxocarbenium Ions: A Case of Ionic Hydrogenation
Lin, Zhenyang,Sun, Yongjie,Wang, Heng,Wen, Jialin,Yang, Tilong,Zhang, Xumu
, p. 6108 - 6114 (2020/03/04)
Ionic hydrogenation has not been extensively explored, but is advantageous for challenging substrates such as unsaturated intermediates. Reported here is an iridium-catalyzed hydrogenation of oxocarbenium ions to afford chiral isochromans with high enantioselectivities. A variety of functionalities are compatible with this catalytic system. In the presence of a catalytic amount of the Br?nsted acid HCl, an α-chloroether is generated in situ and subsequentially reduced. Kinetic studies suggest first-order kinetics in the substrate and half-order kinetics in the catalyst. A positive nonlinear effect, together with the half kinetic order, revealed a dimerization of the catalyst. Possible reaction pathways based on the monomeric iridium catalyst were proposed and DFT computational studies revealed an ionic hydrogenation pathway. Chloride abstraction and the cleavage of dihydrogen occur in the same step.
Enantioselective synthesis of tetrahydroisoquinoline derivatives via chiral-at-metal rhodium complex catalyzed [3+2] cycloaddition
Qurban, Saira,Du, Yu,Gong, Jun,Lin, Shao-Xia,Kang, Qiang
, p. 249 - 252 (2019/01/04)
An asymmetric [3+2] cycloaddition of C,N-cyclic azomethine imines with α,β-unsaturated 2-acyl imidazoles catalyzed by a chiral-at-metal rhodium complex has been developed. The corresponding C-1-substituted tetrahydroisoquinoline derivatives were obtained in high yields (>90%) with excellent stereoselectivities (up to 99% ee and >20?:?1 dr). The reaction can be conducted on a gram-scale using a low catalyst loading (0.5 mol%) with high yield and selectivity.
Synthesis of Tetrahydroisoquinolines through an Iron-Catalyzed Cascade: Tandem Alcohol Substitution and Hydroamination
Marcyk, Paul T.,Cook, Silas P.
, p. 6741 - 6744 (2019/09/07)
Rapid assembly of saturated nitrogen heterocycles - the synthetically more challenging variants of their aromatic relatives - can expedite the synthesis of biologically relevant molecules. Starting from a benzylic alcohol tethered to an unactivated alkene, an iron-catalyzed tandem alcohol substitution and hydroamination provides access to tetrahydroisoquinolines in a single synthetic step. Using a mild iron-based catalyst, the combination of these operations forms two carbon-nitrogen bonds and provides a unique annulation strategy to access this valuable core.
