A mild, efficient and ecofriendly method for synthesis of β-carbolines via Cu-catalyzed aerobic oxidation of 1,2,3,4-tetrahydro-β-carbolines (THβCs) was developed. In addition, this method was successfully applied in the practical total syntheses of perlolyrine and flazin.

The first total synthesis of eudistomin Y7 (7) and total syntheses of eudistomins Y1–Y6 (1–6) are described. An efficient room‐temperature conversion of 1‐benzyl‐3,4‐dihydro‐β‐carbolines (11) into 1‐benzoyl‐β‐carbolines (14) by a one‐pot process of tandem benzylic oxidation and aromatization as the key step of these total syntheses was also studied in detail.

A green chemical method for the conversion of 3,4-dihydro-β-carbolines to β-carbolines has been developed using air as the oxidant. With 15 mol % CuBr 2 as the catalyst, 3,4-dihydro-β-carbolines could be efficiently oxidized to β-carbolines in dimethyl sulfoxide at room temperature in the presence of 1,8-diazabicyclo[5,4,0]undec-7-ene (or Et 3 N). By applying this method, the first total synthesis of 6-hydroxymetatacarboline D was performed through 12 steps in 22% overall yield starting from l -5-hydroxy-tryptophan.

A green and highly stereoselective method for the synthesis of cis or trans-1,3-disubstituted-tetrahydro-β-carbolines has been developed using water as the solvent.

Novel total syntheses of oxoaporphine alkaloids such as liriodenine, dicentrinone, cassameridine, lysicamine, oxoglaucine and O-methylmoschatoline were developed. The key step of these total syntheses is Cu-catalyzed conversion of 1-benzyl-3,4-dihydro-isoquinolines (1-Bn-DHIQs) to 1-benzoylisoquinolines (1-Bz-IQs) via tandem oxidation/aromatization. This novel Cu-catalyzed conversion has been studied in detail, and was successfully used for constructing the 1-Bz-IQ core.