Total synthesis of giffonin H by fluoride-catalyzed macrocyclization

First total synthesis of giffonin H, a highly strained 15-membered macrocyclic diaryl ether, has been achieved. Key steps include Ullmann cross coupling, ( Z )-selective Julia–Kocienski olefination, and fluoride-mediated macrocyclization of TMS-alkyne and aldehyde. The strategy used for macrocyclization is an unprecedented and unique synthetic approach for cyclic diarylheptanoids.