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

Shulei Hu ¹Yu Zhang ²Xiong Xie ³Luhan Li ⁴Kaixian Chen ¹Hong Liu ⁵Jiang Wang²

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作者信息

1. 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
2. State Key Laboratory of Drug Research,Shanghai Institute of Materia Medica,Chinese Academy of Sciences,Shanghai 201203,China;Lingang Laboratoty,Shanghai 200031,China
3. State Key Laboratory of Drug Research,Shanghai Institute of Materia Medica,Chinese Academy of Sciences,Shanghai 201203,China
4. State Key Laboratory of Drug Research,Shanghai Institute of Materia Medica,Chinese Academy of Sciences,Shanghai 201203,China;School of Life Science and Technology,ShanghaiTech University,Shanghai 200031,China
5. 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;School of Life Science and Technology,ShanghaiTech University,Shanghai 200031,China
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Abstract

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.

Key words

C-H functionalization/Rh(Ⅲ)-catalyzed/Alkenylation/Cyclic peptides/Macrolactamization

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出版年

2024

中国化学快报(英文版)

中国化学会

中国化学快报(英文版)

CSTPCDCSCD

影响因子：0.771

ISSN：1001-8417

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