Synthesis of Acerogenin C and (+)-Acerogenin A, Two Macrocyclic Diarylheptanoid Constituents ofAcer nikoense

The macrocyclic ketone acerogenin C (3) and the corresponding alcohol (+)-accerogenin A (1), diarylheptanoid constituents of the maple Acer nikoense were synthesized. The key steps were the selective reduction of the double bond of an α,β-unsaturated ketone (10) and macrocyclization of an iodophenol (13) by a modified Ullmann diarylether synthesis.