The First Total Synthesis of (±)-Arisugacin A, a Potent, Orally Bioavailable Inhibitor of Acetylcholinesterase

Abstract

The first convergent total synthesis of (+/-)-arisugacin A was accomplished by stereoselective construction of the arisugacin skeleton via a Knoevenagel-type reaction of an alpha,beta-unsaturated aldehyde with a 4-hydroxy 2-pyrone and stereoselective dihydroxylation followed by deoxygenation.