Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks

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外文摘要：Heterocycle-braced cyclic peptides have demonstrated enhanced metabolic stability,increased potency and selectivity.Here,we present a rapid synthesis method for constructing Trp(C7)-alkene(E)-crosslinked cyclic peptides with potent anti-proliferative activities against cancer cells,through C-H alkenylation and macrolactamization.This report addresses critical challenges associated with the installation and removal of the directing group N-Piv,configuration selectivity of the olefin,and intramolecular cyclization.No-tably,this method exhibits mild reaction conditions,traceless removal of the directing group,and high configuration selectivity.

外文关键词：

C-H functionalizationRh(Ⅲ)-catalyzedAlkenylationCyclic peptidesMacrolactamization

作者：

Shulei Hu、Yu Zhang、Xiong Xie、Luhan Li、Kaixian Chen、Hong Liu、Jiang Wang

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作者单位：

Department of Medicinal Chemistry,School of Pharmacy,China Pharmaceutical University,Nanjing 211198,China

State Key Laboratory of Drug Research,Shanghai Institute of Materia Medica,Chinese Academy of Sciences,Shanghai 201203,China

Lingang Laboratoty,Shanghai 200031,China

School of Life Science and Technology,ShanghaiTech University,Shanghai 200031,China

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出版年：

2024

DOI：

10.1016/j.cclet.2023.109408

中国化学快报(英文版)

中国化学会

中国化学快报(英文版)

CSTPCD

影响因子：0.771

ISSN：1001-8417

年,卷(期)：2024.35(8)