抗生素Elansolid A简化衍生物的不对称全合成
收稿日期: 2024-01-15
修回日期: 2024-02-26
网络出版日期: 2024-03-21
基金资助
云南省高层次人才计划(Y93D321261); 中国科学院区域发展青年学者项目(E323521311); 及云南省科学技术厅(202305AH34005); 及云南省科学技术厅(202401AS070096)
Asymmetric Total Synthesis towards the Simplified Analogs of Antibiotic Elansolid A
Received date: 2024-01-15
Revised date: 2024-02-26
Online published: 2024-03-21
Supported by
High-Level Talent Program of Yunnan Province(Y93D321261); Regional Development Program for Young Scholars, Chinese Academy of Sciences (CAS)(E323521311); Science and Technology Department of Yunan Province(202305AH34005); Science and Technology Department of Yunan Province(202401AS070096)
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elansolid A的首次全合成. 在此基础上, 提出了elansolid A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： 不对称全合成; 偶联反应; 简化类似物; Elansolid A
杨帅 , 吴杰 , 汪亮亮 . 抗生素Elansolid A简化衍生物的不对称全合成[J]. 有机化学, 2024 , 44(7) : 2350 -2362 . DOI: 10.6023/cjoc202401017
Natural product elansolid A belongs to one type of polyketide macrolactone with promising antibiotic activity. Previously, 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.
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