The first total synthesis of (+/-)-arisugacin A, a potent, orally bioavailable inhibitor of acetylcholinesterase

Toshiaki Sunazuka; Masaki Handa; Kenichiro Nagai; Tatsuya Shirahata; Yoshihiro Harigaya; Kazuhiko Otoguro; Isao Kuwajima; Satoshi Omura

doi:10.1021/ol017046x

The first total synthesis of (+/-)-arisugacin A, a potent, orally bioavailable inhibitor of acetylcholinesterase

Org Lett. 2002 Feb 7;4(3):367-9. doi: 10.1021/ol017046x.

Authors

Toshiaki Sunazuka¹, Masaki Handa, Kenichiro Nagai, Tatsuya Shirahata, Yoshihiro Harigaya, Kazuhiko Otoguro, Isao Kuwajima, Satoshi Omura

Affiliation

¹ The Kitasato Institute and School of Pharmaceutical Sciences, Kitasato University, Tokyo 108-8642, Japan. sunakuzat@pharma.kitasato-u.ac.jp

PMID: 11820881
DOI: 10.1021/ol017046x

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetylcholinesterase / drug effects*
Administration, Oral
Biological Availability
Cholinesterase Inhibitors / chemical synthesis*
Cholinesterase Inhibitors / chemistry
Cholinesterase Inhibitors / pharmacokinetics
Cholinesterase Inhibitors / pharmacology
Molecular Structure
Pyrans / chemistry*
Spectrum Analysis

Substances

Cholinesterase Inhibitors
Pyrans
arisugacin A
Acetylcholinesterase