Total Synthesis of Isohericerinol A and Its Analogues to Access Their Potential Neurotrophic Effects.

The secondary metabolites from are well-known to have neurotrophic and neuroprotective effects. Isohericerinol A (), isolated by our colleagues from its fruiting parts has a strong ability to increase the nerve growth factor secretion in C6 glioma cells. The current work describes the total synthesis of and its regioisomer in a few steps.

Neurotrophic isoindolinones from the fruiting bodies of Hericium erinaceus.

Four compounds, hericerin (1), isohericerinol A (2), N-de-phenylethyl isohericerin (3) and corallocin A (4) were isolated from the fruiting bodies of Hericium erinaceus, a lion's mane mushroom (Hericiaceae). Among them, isohericerinol A (2) was newly reported in nature. Further investigation of the neurotrophic effect of isolated compounds demonstrated that isohericerinol A (2) strongly increased the nerve growth factor (NGF) production in C6 glioma cells followed by corallocin A (4) and hericerin (1).

α-Hydroxy acid as an aldehyde surrogate: metal-free synthesis of pyrrolo[1,2-]quinoxalines, quinazolinones, and other N-heterocycles decarboxylative oxidative annulation reaction.

A metal-free and efficient procedure for the synthesis of pyrrolo[1,2-]quinoxalines, quinazolinones, and indolo[1,2-]quinoxaline has been developed. The key features of our method include the generation of aldehyde from α-hydroxy acid in the presence of TBHP (-butyl hydrogen peroxide), and further condensation with various amines, followed by intramolecular cyclization and subsequent oxidation to afford the corresponding quinoxalines, quinazolinones derivatives in moderate to high yields.

Transition metal-free synthesis of quinazolinones using dimethyl sulfoxide as a synthon.

Biologically important quinazolinones have been synthesized from 2-aminobenzamides and DMSO. The key feature of the reaction is the utilization of DMSO as a methine source for intramolecular oxidative annulation. The CNS depressant drug methaqualone has also been synthesized by our methodology.

An efficient construction of N,N-bicyclic pyrazolidinones comprising enaminonitriles via asymmetric [3+2] cycloaddition.

The first thiourea catalysed asymmetric [3+2] cycloaddition reaction between azomethine imines and malanonitriles was developed. Using this novel synthetic strategy, hybrid molecules containing N,N-bicyclic pyrazolidinones fused with enaminonitriles were synthesized in good yields with excellent enantioselectivities (up to 98% ee).