Synthetic Studies on Hennoxazole A with Antivirus Activity

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Hennoxazoles (A-D) were isolated by Higa and coworkers from the okinawan sponge, Polyfibrospongia sp. Hennoxazole A has been shown to have interesting antivirus and antiinflammatory activities. The compound possesses a stucturally unique bisoxazole adjacent to a tetrahydropyran/hemiketal and a triene. We hoped to synthesis Hennexazole A via three key intermediates, tetrohydropyran, bisoxazole, and triene moieties. Our work concerned with the attempted synthesis of suitably protected forms of tetrohydropyran and triene moieties.The synthesis of the triene starting from methyl (R)-3-hydroxy-2-methylpropionate was accomplished by cross-coupling of the allyl bromide and the vinyltin using palladium.The methyl ketone, the ring opened form of the tetrahydropyran/hemiketal moiety was synthesized from (S)-1,2,4-butanetriol in several steps.Conversion of the above methyl ketone to the tetrahydropyran/hemiketal is actively underway.