Total synthesis and further scrutiny of the in vitro antifungal activity of 6-nonadecynoic acid

The antifungal, naturally occurring acetylenic fatty acid 6-nonadecynoic acid was synthesized in three steps (18% overall yield), for the first time starting with commercially available 1-tetradecyne. The synthesis developed herein will facilitate the further study of the antifungal properties of this naturally occurring acetylenic fatty acid. The 6-nonadecynoic acid exhibited the best antifungal activity (< 4.3 mu M) against Cryptococcus neoformans ATCC 66031 in Sabouraud Dextrose Broth (SDB) media. In our hands, it was not active against Candida albicans ATCC 14053 and Candida albicans ATCC 60193.