A series of homologous <i>C</i>-nucleoside mimics have been synthesized <i>via</i> an efficient and facile synthetic protocol involving the conjugate addition of purine to sugar derived olefinic ester in good yields. The synthesized compounds were evaluated for their antiplasmodial activity <i>in vitro</i> against both the CQ-sensitive and resistant strains of <i>P. falciparum</i>. Interestingly, all the synthesized nucleoside analogs exhibited an IC<sub>50</sub> of <5 μM, while compounds <b>22a</b>, <b>23a</b>, and <b>23b</b> showed promising antiplasmodial activity with an IC<sub>50</sub> of 1.61, 0.88, and 1.01 μM against the CQ-sensitive <i>Pf</i>3D7 strain and 1.14, 1.01, and 2.57 μM against the CQ-resistant <i>Pf</i>K1 strain, respectively.