User talk:Ivan Zhyvolup

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PZQ from enantiopure styrene oxide and aminomethyloxazole

Abstract

The enantioselective de novo synthesis of the important drug praziquantel (PZQ) is described employing (.)-styrene oxide and 2-aminomethyloxazole (or a related compound) as the starting materials.

Introduction

Praziquantel (PZQ) is an important drug used in the worldwide treatment of schistosomiasis (Bilharziosis).[ref] The racemate is universally employed even though it is known that the inactive (S)-enantiomer causes side effects and is responsible for the pill's bitter taste. PZQ remains the only viable drug for the treatment of this burdensome disease, and it is important that the drug is used in a way that postpones any possible development of resistance; one possible treatment regime would be to increase the dose administered while reducing the current large pill size. The World Health Organisation deemed the generation of enantiopure (R)-PZQ to be an important strategic objective. Recently a method was found for the resolution of PZQ that is efficient and inexpensive. Neverthless, despite being economically viable, resolution processes are chemically inefficient in that half the material is discarded and new steps are introduced that covert PZQ to an amine that may be resolved. It was of interest to determine whether asymmetric catalysis might provide a solution to the exclusive synthesis of (R)-PZQ.
PZQ has been synthesised previously using a catalytic, asymmetric approach involving a synthetic intermediate that is not currently employed on a large scale, and the efficiency of the asymmetric step was low.[ref] One obvious possibility is to adapt a known synthesis of PZQ that employs a Pictet-Spengler reaction[ref] but unfortunately such a reaction, employing an aromatic ring lacking electron-donating groups, has never been carried out asymmetrically in the 100-year history of the Pictet-Spengler reaction. A remaining possibility would be to start from rac-PZQ, destroy the stereocentre with an oxidation, then re-install it with an asymmetric hydrogenation.

References

(May be found in the public Mendeley group here, but should also be listed below. Direct links or DOIs in addition to citation please)