title: Total synthesis of solamargine.
abstract: Solamargine, (25R)-3β-{O-α-L-rhamnopyranosyl-(1→2)-[O-α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranosyloxy}-22α-N-spirosol-5-ene, has been synthesized in 13 steps in a 10.5% overall yield starting from the naturally abundant diosgenin. Condensation of a partially protected glucopyranosyl donor with an oxaza-spiro moiety, which was formed in one-pot azido reduction, significantly improved the synthesis of desired molecule. The target compound exhibited good cytotoxic activities against tumor cells HeLa, A549, MCF-7, K562, HCT116, U87, and HepG2 with IC(50) ranging from 2.1 to 8.0 μM.
authors.affiliation: State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences (CAS), Beijing 100085, China.
authors.forename: Guohua
authors.initials: G
authors.lastname: Wei
authors.forename: Jing
authors.initials: J
authors.lastname: Wang
authors.forename: Yuguo
authors.initials: Y
authors.lastname: Du
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D004144:Diosgenin / Q000737:chemistry*; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D012991:Solanaceous Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D012991:Solanaceous Alkaloids; C026609:beta-solamarine; D004144:Diosgenin