Total Synthesis of Lissodendoric Acid A

We describe a full account of our synthetic strategy leading to the first total synthesis of the manzamine alkaloid lissodendoric acid A . These efforts demonstrate that strained cyclic allenes are valuable synthetic building blocks and can be employed efficiently in total synthesis. A synthetic strategy leading to the first total synthesis of lissodendoric acid A is reported. The 12-step synthesis centers on an enantiospecific Diels-Alder cycloaddition of a strained azacyclic allene to construct the core of the natural product. The study demonstrates that strained cyclic allenes are valuable synthetic building blocks for total synthesis. image