Azaanthraquinone assembly from N-propargylamino quinone via a Au(I)-catalyzed 6-endo-dig cycloisomerization

Abstract

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.