垂盆草苷的合成

SYNTHESIS OF SARMENTOSIN

摘要: 目的：垂盆草苷(1)是从垂盆草(Sedum sarmentosum Bunge)中分得的，能降低慢性病毒性肝炎病人血清谷丙转氨酶的活性成分并有免疫调节作用。以1，2，4-丁三醇-1，2-丙缩酮(3)为原料，经8步反应完成其全合成。方法和结果：溴化α-D-四乙酰基吡喃葡萄糖在氧化银和分子筛存在下，与3缩合生成β-葡糖苷4。去缩酮保护后，伯醇基用三苯甲基保护得化合物6。6的仲醇基用PCC氧化成酮7，羰基与丙酮合氰化氢交换得加成物8。氰醇8用氯化亚砜脱水，形成所需的E式双键化合物9。用三甲碘硅烷脱除三苯甲基得烯丙醇10，最后用三乙胺含水甲醇溶液除去乙酰基，得目标产物1。总产率5.8%。结论：首次完成了天然产物垂盆草苷的人工合成。

Abstract: AIM: The synthesis of sarmentosin. METHODS: Condensation of butane-1,2,4-triol-1,2-acetonide(3) with α-D-glucopyranosyl bromide tetraacetate in the presence of Ag2O and molecular sieves gave the desired β-glucoside 4, which was transformed into sarmentosin via a reaction sequence of 7 steps. RESULTS: The overall yield is 5.8%. CONCLUSION: The first synthesis of sarmentosin(1), a potent natural GPT lowering agent, was achieved.