Total synthesis of terfestatins A and B

Abstract Terfestatin A, a specific inhibitor of auxin signaling, has been synthesized from a known aromatic aldehyde in 21% overall yield via five steps. The first total synthesis of terfestatin B with potent neuroprotective activity has also been accomplished in eight steps from the same aromatic aldehyde in 30% overall yield through a common intermediate. The key feature of this synthesis is the utilization of the aldehyde functionality of the starting material both as a directing group for regioselective O-protection and as a masked hydroxy group.