Procedure for the inversion of the sterochemistry at c13 of...

Details Procedure for the inversion of the sterochemistry at c13 of... Procedure for the inversion of the sterochemistry at c13 of...

C - Chemistry, Metallurgy

07

H

C07H 17/08 (2006.01) A01N 43/90 (2006.01) A61K 31/70 (2006.01) C07D 493/22 (2006.01) C07H 19/01 (2006.01)

Patent

CA 2068388

101/DLR51 18342 TITLE OF THE INVENTION PROCEDURE FOR THE INVERSION OF THE STEREOCHEMISTRY AT C13 OF AVERMECTIN AGLYCONE COMPOUNDS ABSTRACT OF THE DISCLOSURE The natural stereochemistry at the 13-position of avermectin aglycones, normally .alpha.-oriented or below the plane of the molecule, is inverted or epimerized into the .beta.-position. The procedure starts with the avermectin aglycone compounds where the 13.alpha.-hydroxy group is substituted with a leaving group. Treatment of the substituted compound with tetra alkyl ammonium nitrate displaces the leaving group, substitutes a nitrate ester or a nitrooxy group, for the hydroxy and inverts the 13-stereochemistry to .beta.. Reduction of the nitrooxy group returns the 13-hydroxy group and retains the 13-.beta. configuration. The intermediate 13-nitrooxy compounds are themselves potent anti-parasitic agents.

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