Synthesis and characterization of the enantiomerically pure cis- and trans-2,4-dioxa-3-fluoro-3-phosphadecalins as inhibitors of acetylcholinesterase.
The title compounds, the P(3)-axially- and P(3)-equatorially-substituted cis- and trans-configured 3-fluoro-2,4-dioxa-3-phosphadecalin 3-oxides (=3-fluoro-2,4-dioxa-3-phosphabicyclo[4.4.0]decane 3-oxides) have been prepared (ee>99%) and fully characterized. The compounds are irreversible inhibitors of acetylcholinesterase, and both the kinetic data and the mechanisms of the inhibition are determined by a novel enzyme-kinetic approach that is described in the preceding report. The inhibitors display pronounced stereoselectivity, and several of them are significantly stronger than diisopropyl fluorophosphate that is generally used as a potent standard.
Wächter
Michael
M
Organisch-chemisches Institut der Universität Zürich, Winterthurerstrasse 190, Zürich.
Rüedi
Peter
P