Bis-α-sulfenylated diketopiperazine derivative corresponding to the monomer of vertihemiptellide A, a potential antituberculosis agent from the insect pathogenic fungus Verticillium hemipterigenum BCC 1499, was synthesized. the method involved the following crucial steps: ⅰ）regioselective nucleophilic addition of Grignard reagent to a tricarbonyl compound; ⅱ）dihydroxylation of a diketopiperazine containing exo-methylene function using oso4 in the presence of phenylboronic acid and N-methylmorpholine N-oxide（NMo）; and ⅲ）α-sulfenylation of a diketopiperazine derivative using 4-methoxybenzyl mercaptan（PMB-Sh）and trifluoroacetic acid（tFA）
