Short syntheses of ( S)-pipecolic acid, ( R)-coniine, and ( S)-δ-coniceine using biocatalytically-generated chiral building blocks

Abstract

The kinetic resolutions of both (±)-N-(benzyloxycarbonyl-2-(hydroxymethyl)piperidine [(±)- 5] and (±)-N-( tert-butoxycarbonyl)-2-(hydroxymethyl)piperidine [(±)- 6] catalyzed by the enzyme acylase I from Aspergillus species (AA-I) afforded the chiral building blocks ( S)- 5 and ( S)- 6, respectively; which were used for the syntheses of the title natural products and derivatives of ( S)-pipecolic acid. The syntheses were short (2–4 steps) and proceeded with satisfactory overall yield.