Methodology-driven efficient synthesis of cytotoxic(±)-piperarborenine B  

作　　者：Chunngai Hui Andrey P.Antonchick 

机构地区：[1]Max Planck Institute of Molecular Physiology,Department of Chemical Biology,Dortmund 44227,Germany [2]Technical University Dortmund,Faculty of Chemistry and Chemical Biology,Dortmund 44221,Germany [3]Nottingham Trent University,School of Science and Technology,Department of Chemistry and Forensics,Nottingham NG118NS,United Kingdom

出　　处：《Green Synthesis and Catalysis》2022年第4期339-348,共10页绿色合成与催化（英文）

基　　金：A.P.A.thanks for the support of the DFG(No.AN 1064/4–1)and the Boehringer Ingelheim Foundation(Plus 3).C.H.thanks the International Max Planck Research School for Living Matter(Dortmund,Germany).

摘　　要：The evolution of synthetic design toward the efficient synthesis of cyclobutane natural product(±)-piperarborenine B is demonstrated.Taking the advantages of good functional group compatibility of contractive synthesis of cyclobutanes from pyrrolidines,stereoselective synthesis of unsymmetric highly functionalized cyclobutanes core of(±)-piperarborenine B was realized in one step.Also,an unprecedented carboxylic acid assisted-diastereoselective Kracho decarboxylation/transmethylation features a new strategy for a non-symmetrical cyclobutane core.The synthesis of(±)-piperarborenine B illustrates the advancement of methodology resulting in the improvement in synthetic efficiency.

关 键 词：CYCLOBUTANE Molecular editing Ring contraction Stereoselective synthesis Protecting group free 

分 类 号：O62[理学—有机化学]