The first total synthesis of (+/-)-arisugacin A, a potent, orally bioavailable inhibitor of acetylcholinesterase.
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.
Sunazuka
Toshiaki
T
The Kitasato Institute and School of Pharmaceutical Sciences, Kitasato University, Tokyo 108-8642, Japan. sunakuzat@pharma.kitasato-u.ac.jp
Handa
Masaki
M
Nagai
Kenichiro
K
Shirahata
Tatsuya
T
Harigaya
Yoshihiro
Y
Otoguro
Kazuhiko
K
Kuwajima
Isao
I
Omura
Satoshi
S
D000110:Acetylcholinesterase / Q000187:drug effects*; D000284:Administration, Oral; D001682:Biological Availability; D002800:Cholinesterase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics / Q000494:pharmacology; D015394:Molecular Structure; D011714:Pyrans / Q000737:chemistry*; D013057:Spectrum Analysis
D002800:Cholinesterase Inhibitors; D011714:Pyrans; C432303:arisugacin A; D000110:Acetylcholinesterase