论文部分内容阅读
目的:垂盆草苷(1)是从垂盆草(SedumsarmentosumBunge)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αD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58%。结论:首次完成了天然产物垂盆草苷的人工合成
OBJECTIVE: Genotyping (1) is obtained from Sedumsarmentosum Bunge and can reduce the active components of serum alanine aminotransferase in patients with chronic viral hepatitis and has immunomodulatory effects. The 1,2,4-butantriol 1,2-budketal (3) was used as the raw material to complete its synthesis by 8-step reaction. Methods and Results: In the presence of silver oxide and molecular sieve, bromine αDtetraacetyl glucopyranose was condensed with 3 to form βglucoside 4 . After the deketal protection, the primary alcohol group is protected with a trityl group to give compound 6. The secondary alcohol group of 6 is oxidized with PCC to ketone 7, and the carbonyl group is exchanged with acetone and hydrogen cyanide to obtain the adduct 8. The cyanohydrin 8 is dehydrated with thionyl chloride to form the desired E-form double bond compound 9. Removal of the trityl group using trimethyl iodide yields allyl alcohol 10, and finally the removal of the acetyl group using triethylamine in aqueous methanol gives the target product 1. The total yield is 58%. Conclusion: For the first time, the synthesis of the natural product ceantidine has been completed.