通过扩环反应生成稠合七元多环体系及其在倍半萜全合成中的应用
Generation of Fused Seven-Membered Polycyclic Systems via Ring Expansion and Application to the Total Synthesis of Sesquiterpenoids.
作者信息
Xing Zhimin, Fang Bowen, Luo Shangwen, Xie Xingang, Wang Xiaolei
机构信息
State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou 730000, China.
Key Laboratory for Utility of Environment-Friendly Composite Materials and Biomass in University of Gansu Province, Gansu Provincial Biomass Function Composites Engineering Research Center, College of Chemical Engineering, Northwest Minzu University, Lanzhou 730030, China.
出版信息
Org Lett. 2022 Jun 10;24(22):4034-4039. doi: 10.1021/acs.orglett.2c01401. Epub 2022 Jun 1.
Seven-membered polycyclic architectures, widely present in natural products and molecular drugs, are challenging synthetic targets. However, methods for synthesizing fused medium-sized bicyclo[..0] ring systems, including the benzo-cycloheptane systems, are still urgent. Herein we describe a base-induced ring expansion as a general strategy to construct a wide range of fused seven-membered ring systems. The application of this method was demonstrated by the efficient total syntheses of two sesquiterpenoids, plecarpenene and plecarpenone, both bearing a fused bicyclo[5.3.0]decane skeleton.
七元多环结构广泛存在于天然产物和分子药物中，是具有挑战性的合成目标。然而，包括苯并环庚烷体系在内的稠合中型双环[..0]环系统的合成方法仍然十分迫切。在此，我们描述了一种碱诱导的扩环反应，作为构建多种稠合七元环系统的通用策略。通过高效全合成两种倍半萜类化合物plecarpenene和plecarpenone证明了该方法的应用，这两种化合物均具有稠合双环[5.3.0]癸烷骨架。
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