denbinobin and ferric-chloride

A total synthesis of denbinobin (1) in seven steps with an overall yield of 10% is reported. This synthesis used an FeCl3-assisted cyclization of stilbene to form a phenanthrene. The poor yields of the decarboxylation and methoxylation steps were improved upon to become essentially quantitative. This scalable methodology was carried out using ordinary laboratory reagents.

Topics: Anthraquinones; Antineoplastic Agents, Phytogenic; Apoptosis; Chlorides; Cyclization; Ferric Compounds; Molecular Structure; Phenanthrenes