Synthesis of pinosylvin and related heartwood stilbenes

Abstract

Pinosylvin dimethyl ether and three other stilbene ethers were prepared by condensing the appropriate diethylbenzylphosphonates with an aromatic aldehyde. Cleavage of pinosylvin dimethyl ether with boron tribromide gave in good yield the monomethyl ether, while fusion with pyridine hydrochloride yielded pinosylvin.