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
Irvin, Thomas Combs
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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 µmol 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.