Two efficient chiral syntheses of 3-hydroxylysine, a naturally occurri
ng 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 catal
yst. The synthesis of (2S,3R)-3-hydroxylysine demonstrates a beta-hydr
oxy amino acid synthesis with the chirality derived from the Sharpless
chiral cis-hydroxylation.