Eight-Step Asymmetric Synthesis of (–)-Berkelic Acid
Eight-Step Asymmetric Synthesis of (–)-Berkelic Acid
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(α)-山楂酸的八步不对称合成
DOI：
10.1055/a-1799-0459
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发表时间：
2022-03
期刊：
影响因子：
--
通讯作者：
Zhou Qianghui
中科院分区：
文献类型：
--
作者：
Yang Zhenjie;Cheng Hong-Gang;Chen Ruiming;Cao Liming;Wei Qiang;Wang Qingqing;Zhou Qianghui
本文报道了（-）-伯克利酸的八步不对称合成。本工作采用Catellani反应/oxa-Michael加成反应合成异色满骨架，采用酸催化脱保护/螺缩醛化反应合成四环骨架中间体，采用镍催化还原偶联反应合成侧链。值得注意的是，在脱保护/螺缩醛化过程中，从具有高度立体控制的单个现有手性中心产生了四个新的立体中心。
We herein report an eight-step asymmetric synthesis of (–)-berkelic acid. This work features a sequential Catellani-type reaction/oxa-Michael addition with epoxides as dual-functionalized alkylating reagents for synthesizing isochroman framework, a one-pot acid-catalyzed deprotection/spiroacetalization process for the construction of tetracyclic core intermediate, and a late-stage Ni-catalyzed reductive coupling reaction for the installation of the side chain. Remarkably, during the deprotection/spiroacetalization process, four new stereocenters are created from a single existing chiral center with high stereocontrol.