A chiron approach towards the synthesis of 3-hydroxy lysine and its derivatives.

Abstract: A general and efficient route towards the synthesis of three derivatives of structurally and functionally important amino acid, lysine is reported. Chemoselective reduction of aldehydic functionality in C-3-azido conjugated aldehyde 4, under Luche condition, is the key step in the synthetic sequence. The lysine derivative, (2S,3R)-2,6-diazido-3-hydroxy-hex-4-ene-oic acid 9 could be used to prepare switch peptide using Staudinger reaction, while the unprotected (2S,3R)-2,6-diamino-3-hydroxy-hexanoic acid hydrochloride 10 is a proven reaction intermediate towards the synthesis of natural product (−)-Balanol. [Copyright &y& Elsevier]