Refernces
10.1021/ja204040k
The research focuses on the enantioselective total synthesis of (-)-Kibdelone C, a naturally occurring compound with significant anticancer activity. The synthesis strategy involves the assembly of the AB-DEF-ring system from an isoquinolinone and a tetrahydroxanthone fragment, which are derived from simpler precursors through a series of chemical reactions. Key steps include a Shi epoxidation to establish stereochemistry, an acid-catalyzed cyclization to form the tetrahydroxanthone, and a C-H arylation to complete the hexacyclic skeleton. Reactants used in the synthesis include amino alcohol, benzoic acid, and various other organic compounds and reagents such as TEMPO, BCl3, and Sonogashira coupling partners. The synthesis process also involves the use of Swern oxidation, Dess-Martin oxidation, and other protective group manipulations. Analytical techniques employed to characterize the intermediates and final product include 1H and 13C NMR spectroscopy, HPLC/MS, and molecular weight determination, confirming the successful replication of (-)-Kibdelone C with optical rotation and spectroscopic data matching those of the natural product.
10.1007/s10593-008-0140-3
The research aimed to efficiently synthesize a series of 3-arylisoquinolin-1(2H)-ones, which are nitrogen analogues of isocoumarins and are found in various bioactive natural products. These compounds have therapeutic value, exhibiting activities such as antidepressant, anti-inflammatory, and analgesic properties. The study focused on converting 3-substituted isocoumarins into their nitrogen analogues by refluxing with methanamide. The process was successful, yielding isoquinolin-1(2H)-ones in 76–85% yield and high purity. The chemicals used in this process included 3-substituted isocoumarins (1a-j) and methanamide, with the reaction progress monitored by TLC, and the products characterized by comparing their mp, IR, 1H NMR, and mass spectral data with those of the corresponding isocoumarins. The conclusion of the research was that a one-pot conversion of 3-substituted isocoumarins to the corresponding isoquinolones was achieved, demonstrating a synthetically feasible procedure for accessing these bioactive heterocycles.
10.1021/ol301131s
The study presents a novel ligand-free palladium-catalyzed cascade reaction for synthesizing highly diverse isoquinolin-1(2H)-one derivatives. The process involves using isocyanides and amide precursors synthesized by Ugi-MCR. The researchers explored a variety of acids, amines, and isocyanides as starting materials for the Ugi-MCR, leading to diverse amide precursors. These precursors then underwent a Pd-catalyzed reaction involving isocyanide insertion and intramolecular cyclization, followed by a Mazurciewicz-Ganesan type sequence. The reaction conditions were optimized with Pd(OAc)? as the catalyst, Cs?CO? as the base, and DMF as the solvent, achieving moderate to good yields of the desired isoquinolin-1(2H)-one derivatives. The study highlights the potential for synthesizing a wide range of biologically active molecules using this method, offering a straightforward and atom-economical approach for combinatorial and medicinal chemistry.