Citation: Shulei Hu, Yu Zhang, Xiong Xie, Luhan Li, Kaixian Chen, Hong Liu, Jiang Wang. Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks[J]. Chinese Chemical Letters, ;2024, 35(8): 109408. doi: 10.1016/j.cclet.2023.109408 shu

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

Shulei Hu ^{a, b} ,
Yu Zhang ^{b, c} ,
Xiong Xie ^b ,
Luhan Li ^{b, d} ,
Kaixian Chen ^{a, b, *,} ,
Hong Liu ^{a, b, d, *,} ,
Jiang Wang ^{b, c, *,}

a.
Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University, Nanjing 211198, China
b.
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
c.
Lingang Laboratoty, Shanghai 200031, China
d.
School of Life Science and Technology, ShanghaiTech University, Shanghai 200031, China

kxchen@simm.ac.cn

hliu@simm.ac.cn

jwang@lglab.ac.cn

Received Date: 18 October 2023
Revised Date: 5 December 2023
Accepted Date: 14 December 2023
Available Online: 19 December 2023

Figures(8)

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. Notably, this method exhibits mild reaction conditions, traceless removal of the directing group, and high configuration selectivity.
- C-H functionalization,
- Rh(Ⅲ)-catalyzed,
- Alkenylation,
- Cyclic peptides,
- Macrolactamization
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