Total Synthesis of Chaxalactin B, a Rare 22‐Membered Macrolactone

Abstract

Chaxalactin B is a rare 22‐membered antibacterial macrolactone isolated from the extremophilic bacterium Streptomyces leeuwenhoekii C34 T collected in the Atacama Desert. Its highly functionalized carbon skeleton, featuring a challenging ( Z / E )‐diene, an all‐ E triene, and four contiguous stereogenic centers, makes it an attractive and challenging synthetic target. We report herein the first total synthesis of chaxalactin B, completed in 23 steps for the longest linear sequence. The synthesis relies on a convergent strategy involving the assembly of two main fragments: C1–C9 and C10–C25. Key features of this strategy include a highly diastereoselective Marshall propargylation to establish the C12–C13 stereocenters, efficient fragment assembly through cross‐coupling reactions, and a late‐stage Shiina macrolactonization to close the 22‐membered macrolactone.

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BibTeX

@article{montiege2026total,
  title = {{Total Synthesis of Chaxalactin B, a Rare 22‐Membered Macrolactone}},
  author = {Ophélie Montiège and Thomas Defuentes and Axelle Berrou and Charlotte Boullier and Frédéric Legros and Catherine Gaulon‐nourry and Anne‐sophie Castanet and Anne‐caroline Chany},
  journal = {ChemistryEurope},
  year = {2026},
  month = oct,
  doi = {10.1002/ceur.70373},
  url = {https://hal.science/hal-05801319v1},
  note = {CC BY 4.0},
}

RIS

TY  - JOUR
TI  - Total Synthesis of Chaxalactin B, a Rare 22‐Membered Macrolactone
AU  - Ophélie Montiège
AU  - Thomas Defuentes
AU  - Axelle Berrou
AU  - Charlotte Boullier
AU  - Frédéric Legros
AU  - Catherine Gaulon‐nourry
AU  - Anne‐sophie Castanet
AU  - Anne‐caroline Chany
PY  - 2026
DA  - 2026/10/13
JO  - ChemistryEurope
DO  - 10.1002/ceur.70373
UR  - https://hal.science/hal-05801319v1
AB  - Chaxalactin B is a rare 22‐membered antibacterial macrolactone isolated from the extremophilic bacterium Streptomyces leeuwenhoekii C34 T collected in the Atacama Desert. Its highly functionalized carbon skeleton, featuring a challenging ( Z / E )‐diene, an all‐ E triene, and four contiguous stereogenic centers, makes it an attractive and challenging synthetic target. We report herein the first total synthesis of chaxalactin B, completed in 23 steps for the longest linear sequence. The synthesis relies on a convergent strategy involving the assembly of two main fragments: C1–C9 and C10–C25. Key features of this strategy include a highly diastereoselective Marshall propargylation to establish the C12–C13 stereocenters, efficient fragment assembly through cross‐coupling reactions, and a late‐stage Shiina macrolactonization to close the 22‐membered macrolactone.
SN  - 2751-4765
ER  -

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