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

• DOI: 10.1021/ol017046x
• Publication Date: 2002-07-26T04:47:33Z
• Authors: Toshiaki Sunazuka; Masaki Handa; Kenichiro Nagai; Tatsuya Shirahata; Yoshihiro Harigaya; Kazuhiko Otoguro; Isao Kuwajima; Satoshi Ōmura
• Keywords: Acetylcholinesterase inhibitor; Orally active

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