Formal synthesis of chelamidine alkaloids and their derivatives.
Rui-Qi LiYu HeYao DingChee-Kiat AngJie-Sheng TianTeck-Peng LohPublished in: Chemical communications (Cambridge, England) (2018)
A concise two-step operation of α-amination of aldehydes and subsequent Friedel-Crafts/Prins-type cyclization towards accessing tetrahydrobenzo[c]phenanthridine and related structures was developed. The reaction displayed a broad substrate scope and good tolerance to a variety of substituents such as different aromatic heterocyclic rings. In addition, the effectiveness of this protocol was also demonstrated in the formal synthesis of homochelidonine and chelamidine.