Phlomisoic acid reacted with methyl-1-deoxy-2,3,4-tri-O-acetyl-1-bromo-α-D-glucopyranuronate to form the 18-O-β-D-(glucuronopyranoside)-6′-O-methyl ester of 15,16-epoxylabda-8(9),13,14-triene. Reductive amination of methyl 16-formyl-15,16-epoxylabda-8(9),13,14-trienoate or this β-D-glucuronopyranoside of 16-formyl-15,16-epoxylabda-8(9),13,14-triene by propargylamine in the presence of NaBH4 gave the corresponding 16-propargylaminomethyl-15,16-epoxylabda-8(9),13,14-trienes. Copper-catalyzed azide-alkyne cycloaddition of the new terpenoid alkynes and the propargylamide of phlomisoic acid with methyl 1-deoxy-2,3,4-tri-O-acetyl-1-azido-α-D-glucopyranuronate synthesized the corresponding labdanoid glucuronides and diglucuronide. Selective screening of the labdanoid triazolylglucuronides identified compounds with analgesic activity in chemical and thermal irritation tests.

中文翻译：

---

呋喃皂甙与葡萄糖醛酸结合物的合成及镇痛活性评价

Phlomisoic acid 与methyl-1-deoxy-2,3,4-tri-O-acetyl-1-bromo-α-D-glucopyranuronate 反应形成 18-O-β-D-(glucuronopyranoside)-6'-O - 15,16-epoxylabda-8(9),13,14-三烯的甲酯。16-formyl-15,16-epoxylabda-8(9),13,14-trienoate 或 16-formyl-15,16-epoxylabda-8(9),13,14 的这种 β-D-吡喃葡萄糖苷的还原胺化在 NaBH4 存在下通过炔丙基胺生成-三烯得到相应的 16-炔丙基氨基甲基-15,16-epoxylabda-8(9),13,14-三烯。铜催化叠氮炔环加成新萜炔和间苯二甲酸的炔丙酰胺与甲基1-脱氧-2,3,4-三-O-乙酰基-1-叠氮基-α-D-吡喃葡萄糖醛酸合成相应的劳丹酸葡萄糖醛酸和二葡糖苷酸。