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8-epi-Liphagal的合成研究
Studies on the Total Synthesis of 8-epi-Liphagal

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文摘 四环杂萜类天然产物Liphagal含有新奇的[6-7-5-6]四环骨架,是磷酸肌醇3-激酶(PI3K)的有效抑制剂之一,可以选择性抑制细胞增殖和促进细胞死亡,在治疗炎症、免疫紊乱、癌症以及心血管疾病中有潜在的医用价值.从廉价的2,4,5-三甲氧基苯甲醛出发,通过Wittig反应、Cu催化的环化反应、选择性氢化、分子内Friedel-Crafts反应,以直线步骤最长7步,8.72%的总收率实现了8-epi-Liphagal高级中间体10的合成.
其他语种文摘 The tetracyclic meroterpenoid natural product (+)-liphagal is one of a number of natural inhibitors of phosphatidylinositol 3-kinase (PI3K), which plays a central role in regulation of cell proliferation, cell survival, adhesion, membrane trafficking, glucose transport and neurite growth. Liphagal also shows inhibitory activity against PI3Kα with an IC50 of 100 nmol?L~(-1) making it as an agent for the treatment of inflammatory and autoimmune disorders as well as cancer and cardiovascular diseases. From a structural point of view, liphagal has an unprecedented [6-7-5-6] tetracyclic skeleton, and has attracted significant attention from the synthetic chemists. Starting from cheap and commercially available 2,4,5-trimethoxylbenzaldehyde and α-ionone, an advanced intermediate 10 for the synthesis of 8-epi-liphagal was achieved in the longest linear 7 steps and 8.72% yield. The key reactions include: Wittig reaction, Cu-catalyzed cyclization, chemoselective hydrogenation and Friedel-Crafts reaction.
来源 化学学报 ,2012,70(21):2232-2235 【核心库】
DOI 10.6023/a12090626
关键词 8-epi-Liphagal ; 天然产物 ; 合成 ; Friedel-Crafts反应 ; 高级中间体
地址

兰州大学化学化工学院, 功能有机分子化学国家重点实验室, 兰州, 730000

语种 中文
ISSN 0567-7351
学科 化学
基金 国家自然科学基金 ;  教育部“111”计划和科技部“973” ;  卫生部重大科技专项
文献收藏号 CSCD:4754942

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