Yonarolide A, an unprecedented furanobutenolide-containing norcembranoid derivative formed by photoinduced intramolecular[2+2] cycloaddition  

作　　者：Yeqing Du Ligong Yao Xuwen Li Yuewei Guo 

机构地区：[1]School of Chinese Materia Medica,Nanjing University of Chinese Medicine,Nanjing 210023,China [2]State Key Laboratory of Drug Research,Shanghai Institute of Materia Medica,Chinese Academy of Sciences,Shanghai 201203,China [3]Drug Discovery Shandong Laboratory,Bohai Rim Advanced Research Institute for Drug Discovery,Yantai 264117,China

出　　处：《Chinese Chemical Letters》2023年第2期420-424,共5页中国化学快报（英文版）

基　　金：financially supported by the National Key Research and Development Program of China (No. 2021YFF0502400);the National Natural Science Foundation of China (Nos. 81991521, 82022069 and 42076099);the Shanghai Rising-Star Program (No. 20QA1411100);“Youth Innovation Promotion Association” of Chinese Academy of Sciences (No. Y202065);the SKLDR/SIMM Project (No. SIMM2103 ZZ-06)。

摘　　要：Eight polycyclic furanobutenolide-containing norcembrane diterpenoids featuring C19 frameworks(1–8)were rapidly recognized and isolated from the Hainan soft coral Sinularia sp. by the HSQC-based small molecule accurate recognition technology. Yonarolide A(1a), featuring an unprecedented 5/6/4/4/7 pentacyclic ring skeleton, was surprisingly obtained as a transformed product by leaving compound 1 under indoor natural light, and was further proved to be a [2 + 2] cycloaddition product of 1 by photochemical reaction. The absolute stereochemistry of 1a and the three known norcembrane diterpenoids 1, 4, and7 were determined by using X-ray diffraction(XRD) analyses. Further, with the aid of XRD analysis, the structure of scabrolide B(2), which was previously reported of possessing 5/6/7 tricyclic skeleton, was firmly revised as 2a with the rare inelegane skeleton featured by the highly oxygenated 5/7/6 tricyclic carbocycle.

关 键 词：Soft coral SINULARIA Norcembranoid PHOTOCYCLOADDITION SMART method 

分 类 号：O621.256.7[理学—有机化学]