In recent years, the sodium polyhydroxysterols sulfated greatly attract the attention of organic chemists and biomedical scientists due to their novel structures and biological activities against cancer and micropathogens. Using natural sterols (1a～1b) as starting materials, sodium 3,6-dihydroxy-5α-sterol 3-sulfateds (6a～6b) were synthesized in 5 steps with a high overall yield. First, 1a～1b were transformed into the corresponding 4-ene-3,6-dione-steroids (2a～2b) via oxidation with pyridinium chlorochromate ( PCC ). The reduction of 2a～2b by NaBH₄ in the presence of NiCl₂ gave 3β-hydroxy-6-oxysteroids (3a～3b). The reaction of 3a～3b with triethylamine-sulfur trioxide complex offered the ammonium 3β-hydroxy-6-oxysteroid sulfateds (4a～4b) and the treatment of 4a～4b by Cation exchange resin 732 (so-dium form) gave the compounds 5a～5b. The 6a～6b were obtained by the reduction of 5a～5b using NaBH₄ as reductive reagent. Using similar synthetic method, sodium 3β,6-dihydroxycholest-4-ene- 3-sulfated (10a) was obtained. The cytotoxicity of 5a～5b and 6a～6b against Hey-1B (human ovarian car-cinoma cell line) cells was investigated. The results showed that 6a had a distinct cytotoxicity (IC₅₀: 48 nmol/mL).

Key words: sterol, sodium sterol sulfated, sodium 3,6-dihydroxysteroid-3-sulfated, synthesis