Total synthesis of the antibiotic 4-hydroxycyclopent-2-en-1-one acrylate derivative EA-2801

The first total synthesis of (±)-EA-2801, a naturally occurring 4-hydroxycyclopent-2-en-1-one acrylate produced by the fungus Trichoderma atroviridae UB-LMA, was achieved The synthesis started from furfuryl alcohol, manufactured industrially from furfural, produced from waste biomass such as corncobs or sugar cane bagasse. (±)-EA-2801 was synthesized in 5 steps and 71% overall yield starting from 4-hydroxycyclopent-2-en-1-one. Enantio-pure (R)- and (S)-EA-2801 were obtained from racemic mixture by preparative chiral supercritical fluid chromatography (SFC).