Asymmetric Synthesis of ent-Fissistigmatin C.
Asymmetric Synthesis of ent-Fissistigmatin C.
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DOI：
10.1021/acs.orglett.0c03766
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发表时间：
2020-12
期刊：
影响因子：
5.2
通讯作者：
Dongyang Xu;Jiadong Hu;Lee Chen;Luxin Chen;Jiang Su;Jinjin Yang;Siyu Deng;Hongli Zhang;W. Xie
中科院分区：
文献类型：
--
作者：
Dongyang Xu;Jiadong Hu;Lee Chen;Luxin Chen;Jiang Su;Jinjin Yang;Siyu Deng;Hongli Zhang;W. Xie
对映-裂豆豆素C的不对称合成在12个步骤中连续完成（最长线性序列（LLS））。在协同有机催化剂的作用下，通过脂肪醛与2-羟基查尔酮的不对称偶联反应，立体选择性地建立了对映异构体fissistigmatin C在类黄酮和倍半萜片段之间的关键连接。在该合成中还出现了前所未有的最后阶段自由基级联反应，这使得通过在一步中锻造两个连续的C-C键同时建立反式十氢萘框架。
The asymmetric synthesis of ent-fissistigmatin C is successively accomplished in 12 steps (longest linear sequence (LLS)). Relying on the enantioselective coupling of aliphatic aldehyde with 2-hydroxychalcone promoted by cooperative organocatalysts, the pivotal linkage of ent-fissistigmatin C between the flavonoid and the sesquiterpenoid fragment was stereoselectively established. An unprecedented final-stage radical cascade was also featured in this synthesis, which enabled the simultaneous establishment of the trans-decalin framework via forging two consecutive C-C bonds in one step.