Two Chiral Syntheses of threo-3-Hydroxylsine

Abstract

Two efficient chiral syntheses of 3-hydroxylysine, a naturally occurring amino acid and a putative intermediate in the synthesis of balanol, a potent protein kinase C inhibitor, are described. The synthesis of (2R,3S)-3-hydroxylysine utilizes Hayashi's chiral ferroceno gold catalyst. The synthesis of (2S,3R)-3-hydroxylysine demonstrates a β-hydroxy amino acid synthesis with the chirality derived from the Sharpless chiral cis-hydroxylation