An asymmetric total synthesis of ent-ancistrocladinium A was developed via chiral phosphoric acid-catalyzed asymmetric reductive amination of 1-aryl-2-propanone and naphthylamine followed by a Bischler–Napieralski reaction. Direct use of the naphthyl moiety in the amine as a key building block in the natural product allowed us to achieve the total synthesis of ancistrocladinium A in only three steps from the known starting materials. (Figure presented.).
- ancistrocladinium A
- chiral phosphoric acid catalysis
- naphthylisoquinoline alkaloids
- reductive amination
- total synthesis
ASJC Scopus subject areas
- Organic Chemistry