新型螺环苯并呋喃酮-六氢山酮素-吡啶类化合物的非对映选择性合成  

Diastereoselective Synthesis of Novel Spirobenzofuran-hexahydroxanthone-pyridine Hybrids

作　　者：王维娜 张磊[1] 刘雄利[1] 张敏[1] 彭礼军[1] WANG Wei-na;ZHANG Lei;LIU Xiong-li;ZHANG Min;PENG Li-jun(National & Local Joint Engineering Research Center for the Exploition of Homology Resources ofMedicine and Food, Guizhou University, Guiyang 550025, China)

机构地区：[1]贵州大学西南药食两用资源开发利用技术国家地方联合工程研究中心,贵州贵阳550025

出　　处：《合成化学》2021年第12期1083-1089,共7页Chinese Journal of Synthetic Chemistry

基　　金：贵州大学培育项目(202078)。

摘　　要：以苯并呋喃酮-色酮合成子与吡啶查尔酮为原料,在DBU催化下,在二氯甲烷中发生Michael/Michael加成关环反应,非对映选择性合成了11个未见文献报道的螺环苯并呋喃酮-六氢山酮素-吡啶类化合物(3a~3k),产率为46%~65%,dr值为6/1~11/1,其结构经^(1)H NMR,^(13)C NMR和HR-MS(ESI-TOF)表征,并进一步通过单晶确定化合物3g的相对构型。结果表明:该类化合物含有连续5个立体中心,以及一个具有潜在生物活性的六氢山酮素骨架和苯并呋喃酮骨架,可以为生物活性筛选提供物质基础。Eleven novel spirobenzofuran-hexahydroxanthone-pyridine hybrids(3a~3k)were diastereoselectively synthesized via a DBU-catalyzed Michael/Michael cycloaddition of benzofuranone-chromone synthons with pyridinchalones 2 under room temperature conditions in CH_(2)Cl_(2) for 12 h.The yields and dr of 3a~3k were 46%~65%and 6/1~11/1,respectively.The structures of products were characterized by ^(1)H NMR,^(13)C NMR and HR-MS(ESI-TOF).The configuration of compound 3g was further determined by the single crystal.These compounds bear five contiguous stereogenic centers,including a potential bioactive hexahydroxanthin skeleton and benzofuranone skeleton,which can provide a material basis for bioactivity screening.

关 键 词：苯并呋喃酮-色酮合成子 吡啶查尔酮 Michael/Michael反应 螺环苯并呋喃酮-六氢山酮素-吡啶 合成 非对映选择性 

分 类 号：O626.13[理学—有机化学] O623.7[理学—化学]