Applications of aryl isothiocyanates in one-pot elimination reactions, synthesis and anti-oxidant activity of several novel capsiates and progress towards the total synthesis of three icetexane and one noricetexane diterpenoids

An alternative to the Chugaev reaction has been developed. This new method utilizes aryl isothiocyanates in a one-pot elimination process and gives yields comparable to the Chugaev reaction. Additionally, this new procedure eliminates a purification step. Forty-four novel capsiates were prepared from vanillyl alcohol and the corresponding carboxylic acid. The capsiates were tested for anti-oxidant activity by an ORAC assay. Eight capsiates exhibited ORAC values above 5,000 mol Trolox/gram. The first total synthesis of rosmaridiphenol has been completed using a cyclialkylation strategy. The progress towards the total syntheses of salvimultine, perovskone B, and hydrangenone is presented as well.