Azaanthraquinone assembly from N-propargylamino quinone via a Au(I)-catalyzed 6-endo-dig cycloisomerization.
A methodology to assemble the azaanthraquinone skeleton from N-propargylamino quinone by a Au(I)-catalyzed 6-endo-dig cycloisomerization was developed. The catalytic process was applied to the synthesis of alkaloid cleistopholine and its analogues. A mechanism involving benign nucleophilicity of the aminoquinone was proposed.
Jiang
Chunhui
C
School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, P. R. China.
Xu
Min
M
Wang
Shaozhong
S
Wang
Huaqin
H
Yao
Zhu-Jun
ZJ
D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D016227:Benzoquinones / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D007536:Isomerism; D015394:Molecular Structure
D000880:Anthraquinones; D001372:Aza Compounds; D016227:Benzoquinones; C004532:quinone; D006046:Gold