Synthesis of Ahod Moiety of Ralstonin A Using Amino Acid Schiff Base Ni(II)‐Complex Chemistry

Abstract Reported here is the asymmetric synthesis of N ‐Boc‐protected (2 S ,3 S )‐3‐amino‐2‐hydroxyoctadecanoic acid, a component of ralstonin A and ralstoamide A. Key synthetic steps include alkylation of chiral Ni(II) complex of glycine Schiff base, conversion of COOH to keto acid (CO−COOH) and reduction of the carbonyl group to generate α ‐hydroxy functionality. The structure and absolute configuration of (2 S ,3 S )‐ N ‐Boc‐3‐amino‐2‐hydroxyoctadecanoic acid was shown to be identical to that of the naturally occurring compound.