组合化学
环加成
自由基环化
表面改性
对映选择合成
天然产物
继电器
作者
Yibin Xue,Guangbin Dong
摘要
Herein, we describe the first total synthesis of sesquiterpene penicibilaenes A and B through a C-C/C-H approach. In the stage, the Rh-catalyzed cut-and-sew transformation between trisubstituted alkene and cyclobutanone has been employed to construct the unique tricyclo[6.3.1.01,5]dodecane skeleton and the all-carbon quaternary center. Critical linker and Lewis acid effects have been identified for the C-C activation process. In the C-H stage, a desaturation relay-based strategy involving consecutive ketone α,β-dehydrogenation and β-functionalization has been adopted to introduce the 1,3,5-triad stereocenters to the core. The synthesis of penicibilaenes A and B has been completed in 13 and 14 steps, respectively, in the longest linear sequence.
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