An efficient synthesis of naturally occurring tigogenin triglycoside 1a and its three derivatives 1b-d bearing different carbohydrate moieties, as well as their antitumor activities, is described. Partially protected thiogalactosides bearing unprotected 2,4-OH or 4-OH groups were used to facilitate regioselective reactions for one-pot sequential multi-step glycosylation, which has significantly simplified the target molecule synthesis. The synthetic saponins 1a-d exhibited much higher anti-tumor activities than the positive control cisplatin against the human epithelial cervical cancer cell (HeLa) as evaluated by CCK-8 assay.
Keywords: Antitumor activity; One-pot sequential glycosylation; Saponin; Thioglycoside.
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