Efficient total synthesis of three alpinoids via the Au(I)-catalyzed Meyer-Schuster rearrangement.

The total syntheses of three structurally related natural products, deoxyalpinoid B, deoxyalpinoid A, and alpinoid F, are reported, and each features a Au(I)-catalyzed Meyer-Schuster rearrangement as the key step. The synthesis of alpinoid F is reported for the first time. The syntheses of these natural products, all of which exhibit potent anticancer activity, are readily amenable to the preparation of structural analogs.