Synthesis of stryphnoside A, a triterpene saponin isolated from the pericarps of Stryphnodendron fissuratum.

Stryphnoside A, α-l-rhamnopyranosyl 3β-O-[α-l-arabinopyranosyl-(1→4)-β-d-xylopyranosyl-(1→2)-β-d-glucopyranosyl]-2α-hydroxyolean-12-en-28-oate, has been synthesized in 11 steps in 15% overall yield starting from the naturally abundant oleanolic acid. Condensation of a partially protected glucopyranosyl donor and 2α,3β-dihydroxyolean-12-en-28-oic acid derivative using inverse glycosylation procedure has significantly simplified the target saponin synthesis. Stryphnoside A exhibited weak cytotoxic activities against tumor cells HeLa, A549, and HepG2 with IC(50) at mM level.