树豆酮酸B的全合成  

Total Synthesis of Cajanonic Acid B

作　　者：殷智鑫 许小婷 郭兵 汤磊 王建塔 范菊娣 YIN Zhi-xin;XU Xiao-ting;GUO Bing;TANG Lei;WANG Jian-ta;FAN Ju-di(College of Pharmacy,Guizhou Medical University,Guiyang 550004;Guizhou Provincial Engineering Technology Research Center for Chemical Drug R&D,Guiyang 550004,China;Guizhou Provincial Key Laboratory of Pathogenesis and Drug Research on Common Chronic Diseases,Guiyang 550004,China)

机构地区：[1]贵州医科大学药学院,贵州贵阳550004 [2]贵州省化学合成药物研发利用工程技术研究中心,贵州贵阳550004 [3]贵州省常见慢性病发病机制和药物研究重点实验室,贵州贵阳550004

出　　处：《化学试剂》2022年第11期1690-1694,共5页Chemical Reagents

基　　金：国家自然科学基金资助项目(81660573);贵州省普通高等学校科技拔尖人才支持计划项目(黔教合KY字[2017]072);贵州省研究生科研基金项目(黔教合YJSCXJH[2020]148);贵州省高层次创新型人才培养“百”层次人才项目(黔科合人才[2016]4015号)。

摘　　要：树豆酮酸B显示出良好的过氧化物酶体增生物激活受体γ拮抗活性,具有潜在抗糖尿病的生物活性。以4-甲氧基水杨酸甲酯为起始原料,经Williamson醚化、O[1,3]迁移和Claisen重排一锅反应、酚羟基甲基化保护、酯水解、C—H活化/环合级联反应、选择性脱甲基、水解6步反应合成树豆酮酸B,总收率为18.2%,化合物结构经^(1)HNMR、^(13)CNMR和ESI-HRMS表征,与目标产物相符。报道树豆酮酸B的全合成路线,为树豆酮酸B的开发应用奠定了基础。Cajanonic acid B exhibites good antagonistic activity on peroxisome proliferator activated receptor γ and has potential anti diabetic biological activity.Cajanonic acid B was synthesized from methyl 4-methoxysalicylate via one pot reaction of Williamson etherification, O[1,3]-Migration and Claisen rearrangement, hydroxy protection, ester hydrolysis, C—H activation/annulation cascade reactions, selective demethylation, and hydrolysis with an overall yield of 18.2%.The chemical structure of synthesized compound was confirmed by ^(1)HNMR,^(13)CNMR and ESI-HRMS,consistenting with the target product.The synthetic route of cajanonic acid B was reported, and laided a foundation for the development and application of cajanonic acid B.

关 键 词：树豆酮酸B 糖尿病 CLAISEN重排 C—H活化/环合级联反应 全合成 

分 类 号：TQ460[化学工程—制药化工]