Reductive cleavage of the trichlorethyl ester (X) using zinc powder and ammonium acetate gave acid (XI). This was then coupled to O-benzyl hydroxylamine in the presence of diethylphosphoryl cyanide (DEPC) to afford hydroxamate (XII). After deprotection of the tert-butyl ester group of (XII), the resultant acid (XIII) was converted to amide (XIV) by DEPC-mediated coupling with methylamine. The title compound was finally obtained by catalytic hydrogenolysis of the protected precursor (XIV) in the presence of Pd/C.

Acylation of the chiral oxazolidinone (I) with undecanoyl chloride furnished the N-acyl oxazolidinone (II). The lithium enolate of (II) was diastereoselectively alkylated with tert-butyl bromoacetate (III) producing (IV) as the major isomer. Then, removal of the chiral auxiliary of (IV) with lithium benzyloxide yielded benzyl ester (V). Acidic cleavage of the tert-butyl ester group of (V) provided carboxylic acid (VI), which was subsequently converted to the trichloroethyl ester (VII) via formation of the corresponding acid chloride, followed by treatment with trichloroethanol. After removal of the benzyl ester group of (VII) by hydrogenolysis, chlorination by means of oxalyl chloride gave acid chloride (VIII). This was then coupled with the protected (S)-perhydropyrazine-3-carboxylic acid (IX) to afford amide (X).