A Modular Synthesis of Antitumor Macrolide (-)-Lasonolide A  

作　　者：Lin Yang Zuming Lin Kuan Zheng Luyao Kong Ran Hong 

机构地区：[1]CAS Key Laboratory of Synthetic Chemistry of Natural Substances,Center for Excellence in Molecular Synthesis,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,345 Lingling Road,Shanghai 200032,China [2]University of Chinese Academy of Sciences,19A Yuquan Road,Beijing 100049,China

出　　处：《Chinese Journal of Chemistry》2020年第7期725-736,共12页中国化学（英文版）

基　　金：the Drug Innovation Major Project(2018ZX09711001-005);the National Natural Science Foundation of China(91856202);the National Key R&D Program of China(2019YFA09005000);the Strategic Priority Research Program(XDB20000000);the Key Research Program of Frontier Sciences(QYZDYSSWSLH026)of the Chinese Academy of Sciences is highly appreciated.We also thank Jie Sun(SIOC,CAS)for the X-ray analysis.

摘　　要：Lasonolide A was identified as a potent antitumor macrolide towards various cancer cell lines.The two tetrahydropyrans bearing multiple stereogenic centers as well as the polyvene linkage attracted a dozen synthetic research groups to launch the total syn-thesis.Based on the synthetic methods developed in our group,namely,the hydroboration of allene and its subsequent allylation as well as the iterative hydroboration of allene and oxidation,the polyol subunits were efficiently constructed and then integrated into the final target.A new Julia olefination reagent,double-headed sulfone,was designed to promote the rapid coupling of two aldehydes bearing multiple functional groups to secure the whole carbon framework.Another highlight of our approach is the application of a traceless protecting group,9-BBN(9-borabicyclo[3.3.1]nonane),to hide the secondary alcohol for debenzylation,and for the first time,to mask the carboxylic acid for Julia olefination under strong basic conditions.

关 键 词：ALDEHYDES LINKAGE REAGENT 

分 类 号：O62[理学—有机化学]