A synthetic study on antiviral and antioxidative chromene derivative

An efficient synthesis of the antiviral and antioxidative chromene (1) was achieved. A small amount of chromene 1 could be derived from plastoquinones 2 and 3, the major constituents of the brown alga, Sargassum micracanthum. By the following synthetic scheme involving its application, many kinds of analogs can be synthesized for evaluation of their biological activity and mechanistic study. The total synthesis of 1, started from geranyl acetate and protected 2-bromo-6-methylhydroquinone, was executed with Sharpless asymmetric dihydroxylation for introduction of the terminal diol system and base-catalyzed sigmatropic rearrangement for construction of the chromene skeleton as the crucial steps. The stereochemistry at C-11' was reconfirmed by this synthesis.