Enantioselective total synthesis of pinnaic acid and halichlorine.

  title={Enantioselective total synthesis of pinnaic acid and halichlorine.},
  author={Shu Xu and Daisuke Unabara and Daisuke Uemura and Hirokazu Arimoto},
  journal={Chemistry, an Asian journal},
  volume={9 1},
The enantioselective total synthesis of the bioactive marine natural products pinnaic acid and halichlorine is reported in detail. Our total synthesis features the construction of the five-membered ring and C9 and C13 stereogenic centers through a palladium-catalyzed trimethylenemethane [3+2] cyclization; the installation of the nitrogen atom through a regioselective Beckmann rearrangement of a poorly reactive ketone; the stereoselective cyclization of the spiro ring through a four-step, one… CONTINUE READING