Total Synthesis of Hinckdentine A

The total synthesis of (+/-)-hinckdentine A is described herein. A cyanide-catalyzed imino-Stetter reaction of the aldimine derived from ethyl 2-amino-3,5-dibromocinnamate and 5-bromo-2-nitrobenzaldehyde followed by oxidative rearrangement afforded a 2,2-disubstituted 3-indolinone derivative containing the carbon skeleton and all of the functional groups present in the natural product correctly positioned, including three bromine atoms. Subsequent D-ring formation and seven-membered C-ring construction completed the total synthesis of hinckdentine A.

Automated summary

The total synthesis of (+/-)-hinckdentine A was achieved through a cyanide-catalyzed imino-Stetter reaction and oxidative rearrangement, followed by D-ring formation and seven-membered C-ring construction. The newly synthesized compound contains all functional groups correctly positioned in the natural product.