Total synthesis of A-315675 based on the cascade Overman rearrangement

The chiral and stereoselective total synthesis of A-315675 1, an antiinfluenza agent, is described. The vicinal diamino moiety in 1 was stereoselectively constructed by the cascade Overman rearrangement of a vicinal allylic-homoallylic diol derived from d-tartrate.

The chiral and stereoselective total synthesis of A-315675 1, an antiinfluenza agent, is described. The vicinal diamino moiety in 1 was constructed in a one-step reaction by the cascade sequential Overman rearrangement of a vicinal allylic-homoallylic diol derived from d-tartrate.