Synthesis of (+)-Brefeldin A

Significance

(+)-Brefeldin A, a metabolite of the fungus Eupenicillium brefeldianum, is an inhibitor of intracellular protein transport. It specifically and reversibly blocks protein transport to the Golgi apparatus, thus becoming an important tool for cell biologists. The synthesis features an intramolecular cyclization to form the five-membered ring core (C → D) and a Rh-catalyzed Michael addition (E + F → G).