A simple synthesis of 1,2-dithiolan-3-ones from
,
-unsaturated thiophenyl esters is reported. Introductionof the biologically active 1,2-dithiolan-3-one-1-oxide moiety of leinamycin into
aldehydo-
D-arabinose
11,the uridine derivative
16, and the deoxythymidine
21 was established. An extended bioactive part ofleinamycin carrying a carbon-carbon triple bond was also synthesized. All of these analogues of leinamycinshowed cytotoxic activity against HeLa3 tumor cells. Interestingly, the lipophilic, silyl group-containingderivatives proved to be more active than the hydrophilic counterparts.