A concise synthesis of the antifungal agent (+)-preussin

A five-step synthetic strategy helps prepare the antifungal agent (+)-preussin from t-Boc-(S)-phenylalanine. The stereoselective synthesis of (+)-preussin involves a Hg(II)-mediated 5-endo-dig ring closure of a ynone. Examination of (+)-preussin with a strain of Saccharomyces cerevisiae, which is deficient in recombinational DNA repair, reveals pressuin to be a DNA damaging agent in yeast.