Asymmetric Total Synthesis towards the Simplified Analogs of Antibiotic Elansolid A  

抗生素Elansolid A简化衍生物的不对称全合成

作　　者：Yang Shuai Wu Jie Wang Liangliang 杨帅;吴杰;汪亮亮(中国科学院昆明植物研究所、植物化学与西部植物资源持续利用国家重点实验室,昆明650201;中国科学院大学,北京101408)

机构地区：[1]State Key Laboratory of Phytochemistry and Plant Resources in West China,Kunming Institute of Botany,Chinese Academy of Sciences,Kunming 650201 [2]University of Chinese Academy of Sciences,Beijing 101408

出　　处：《有机化学》2024年第7期2350-2362,共13页Chinese Journal of Organic Chemistry

基　　金：Project supported by the High-Level Talent Program of Yunnan Province(No.Y93D321261);the Regional Development Program for Young Scholars,Chinese Academy of Sciences(CAS)(No.E323521311);the Science and Technology Department of Yunan Province(Nos.202305AH34005,202401AS070096)。

摘　　要：Natural product elansolid A belongs to one type of polyketide macrolactone with promising antibiotic activity.Pre-viously,the first total synthesis of elansolid A in 28 longest linear sequence(LLS)and 41 steps in total has been achieved.Herein,the simplified analog of elansolid A,featured with a cyclohexyl-fused 19-memebered macrolactone,was proposed,and its asymmetric total synthesis based on a convergent strategy and key reactions exemplified by desymmetric alcoholysis of anhydride,Pd-catalyzed Stille coupling,Suzuki-Miyaura coupling as well as Mukaiyama macrolactonization was finished.Elansolid A属于一类聚酮大环内酯天然产物,具有良好的抗菌活性.已经通过28步的最长线性合成步和总共41步反应实现了elansolidA的首次全合成.在此基础上,提出了elansolidA的简化类似物结构,主要包含环己基稠合的19元大环内酯单元,并采用汇聚式合成策略,通过酸酐的去对称化醇解、钯催化的Stille偶联、Suzuki-Miyaura偶联以及Mukaiyama环化等关键反应,完成了此简化衍生物的不对称全合成.

关 键 词：asymmetric total synthesis coupling reaction simplified analog elansolid A 

分 类 号：O621.3[理学—有机化学]