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Asymmetric total synthesis of polycyclic xanthenes and discovery of a WalK activator active against MRSA
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Journal Article
Asymmetric total synthesis of polycyclic xanthenes and discovery of a WalK activator active against MRSA
2024
Overview
The development of new antibiotics continues to pose challenges, particularly considering the growing threat of multidrug-resistant
Staphylococcus aureus
. Structurally diverse natural products provide a promising source of antibiotics. Herein, we outline a concise approach for the collective asymmetric total synthesis of polycyclic xanthene myrtucommulone D and five related congeners. The strategy involves rapid assembly of the challenging benzopyrano[2,3-a]xanthene core, highly diastereoselective establishment of three contiguous stereocenters through a
retro
-hemiketalization/double Michael cascade reaction, and a Mitsunobu-mediated chiral resolution approach with high optical purity and broad substrate scope. Quantum mechanical calculations provide insight into stereoselective construction mechanism of the three contiguous stereocenters. Additionally, this work leads to the discovery of an antibacterial agent against both drug-sensitive and drug-resistant
S. aureus
. This compound operates through a unique mechanism that promotes bacterial autolysis by activating the two-component sensory histidine kinase WalK. Our research holds potential for future antibacterial drug development.
Structurally diverse natural products are a promising source of antibiotics. Here, the authors report the collective asymmetric total synthesis of polycyclic xanthene myrtucommulone D and five related congeners and discover a compound active against both drug-sensitive and drug-resistant
Staphylococcus aureus
.
Publisher
Nature Publishing Group UK,Nature Publishing Group,Nature Portfolio
Subject
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/ 45/29
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/ Anti-Bacterial Agents - chemical synthesis
/ Anti-Bacterial Agents - chemistry
/ Anti-Bacterial Agents - pharmacology
/ Antiinfectives and antibacterials
/ Humanities and Social Sciences
/ Kinases
/ Methicillin-Resistant Staphylococcus aureus - drug effects
/ Polycyclic Compounds - chemical synthesis
/ Polycyclic Compounds - chemistry
/ Polycyclic Compounds - pharmacology
/ Reagents
/ Science
/ Xanthene
