Au-Catalyzed 1,3-Acyloxy Migration/Cyclization Cascade:A Direct Strategy toward the Synthesis of Functionalized Abietane-Type Diterpenes  

作　　者：Tian-Lu Zheng Si-Zhan Liu Chen-Yu Huo Jing Li Bo-Wen Wang Da-Ping Jin Fu Cheng Xiao-Ming Chen Xiao-Ming Zhang Xue-Tao Xu Shao-Hua Wang 

机构地区：[1]School of Pharmacy&State Key Laboratory of Applied Organic Chemistry,Lanzhou University,Lanzhou 730000 [2]School of Biotechnology and Health Science,Wuyi University,Jiangmen 529020

出　　处：《CCS Chemistry》2021年第11期2795-2802,共8页中国化学会会刊（英文）

基　　金：supported by the National Natural Science Foundation of China(nos.21472077 and 21772071);Department of Education of Guangdong Province(nos.2017KTSCX185,2017KSYS010,2016KCXTD005,and 2019KZDXM035).

摘　　要：A direct strategy toward the synthesis of functionalized abietane-type diterpenes and related polycyclic molecules was developed through an Au-catalyzed 1,3-acyloxy migration/cyclization/electrophilic aromatic substitution cascade.Unlike the known polyene-type cyclization strategies for the construction of abietane-type diterpene skeletons,propargylic ester groups were used for the cyclization process,which can readily lead to the key skeleton with C2 and C3 functionalization.As a demonstration of the potential application of this tandem reaction,a collective total synthesis of(±)-2-ketoferruginol,(±)-fleuryinol B,(±)-salviol,(±)-2β-acetoxyferruginol,and(±)-2β-acetoxysugiyl methyl ether was achieved.Among these molecules,(±)-fleuryinol B and(±)-2β-acetoxyferruginol were synthesized for the first time.

关 键 词：polyene cyclization Au catalysis tandem reaction DITERPENE propargylic ester 

分 类 号：O62[理学—有机化学]