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Peer-reviewedCC BY-NC 3.0Chemical Science

Total synthesis of cochinmicin I and V

  • Jade C. Williams1
  • Preston C. Gourville1
  • Chase K. Pyrah1
  • William J. Stark1
  • Jade A. Bing1
  • Jeffrey N. Johnston1
  1. 1Department of Chemistry, Vanderbilt Institute of Chemical Biology, Vanderbilt University Nashville Tennessee 37235 USA
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Abstract

A total synthesis of the macrocyclic depsipeptides nat-(−)-cochinmicin I and nat-(+)–cochinmicin V is reported. A key feature of all known cochinmicins is a macrocycle feature formed by the C-terminal 3,5-dihydroxy phenyl glycinamide (Dpg7) to a conserved d-allo-threonine residue (i → i + 4). Both epimers of the macrocyclic ester are natural products (cochinmicins I and V). Here we report an approach using Umpolung Amide Synthesis (UmAS) to avoid risk of epimerization at the d-Dpg6 residue. The Mioskowski–Nef reaction is used to divert a nitroalkane common to both Dpg residues toward ester formation between Dpg7 and the d-allo-threonine residue.

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Cite

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BibTeX
@article{williams2026total,
  title = {{Total synthesis of cochinmicin I and V}},
  author = {Jade C. Williams and Preston C. Gourville and Chase K. Pyrah and William J. Stark and Jade A. Bing and Jeffrey N. Johnston},
  journal = {Chemical Science},
  year = {2026},
  month = nov,
  doi = {10.1039/d6sc05662h},
  url = {https://doi.org/10.1039/d6sc05662h},
  note = {CC BY-NC 3.0},
}
RIS
TY  - JOUR
TI  - Total synthesis of cochinmicin I and V
AU  - Jade C. Williams
AU  - Preston C. Gourville
AU  - Chase K. Pyrah
AU  - William J. Stark
AU  - Jade A. Bing
AU  - Jeffrey N. Johnston
PY  - 2026
DA  - 2026/11/05
JO  - Chemical Science
DO  - 10.1039/d6sc05662h
UR  - https://doi.org/10.1039/d6sc05662h
AB  - A total synthesis of the macrocyclic depsipeptides nat-(−)-cochinmicin I and nat-(+)–cochinmicin V is reported. A key feature of all known cochinmicins is a macrocycle feature formed by the C-terminal 3,5-dihydroxy phenyl glycinamide (Dpg7) to a conserved d-allo-threonine residue (i → i + 4). Both epimers of the macrocyclic ester are natural products (cochinmicins I and V). Here we report an approach using Umpolung Amide Synthesis (UmAS) to avoid risk of epimerization at the d-Dpg6 residue. The Mioskowski–Nef reaction is used to divert a nitroalkane common to both Dpg residues toward ester formation between Dpg7 and the d-allo-threonine residue.
SN  - 2041-6520
SN  - 2041-6539
ER  -