Enantioselective Synthesis of Sealutomicin C

Astle SM, Guggiari S, Frost JR, Hepburn HB, Klauber DJ, Christensen KE, Burton JW

The sealutomicins are a family of anthraquinone antibiotics featuring an enediyne (sealutomicin A) or Bergman-cyclized aromatic ring (sealutomicins B–D). Herein we report the development of an enantioselective organocatalytic method for the synthesis of dihydroquinolines and the use of the developed method in the total synthesis of sealutomicin C which features a transannular cyclization of an aryllithium onto a γ-lactone as a second key step.