ArticleNature chemistry2022
Total synthesis of structurally diverse pleuromutilin antibiotics.
Article in Nature chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 10 papers.
What it found
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Who cites it
10 citing papers in PubMed.
- Review
- From Natural Products to Small Molecules: Recent Advancements in Anti-MRSA Therapeutics.ACS medicinal chemistry letters · 2025Review
- Catalyst-controlled directing group translocation in the site selective C-H functionalization of 3-carboxamide indoles and metallocarbenes.Nature communications · 2025Article
- Advances, opportunities, and challenges in methods for interrogating the structure activity relationships of natural products.Natural product reports · 2024Review
- Structural basis of Cfr-mediated antimicrobial resistance and mechanisms to evade it.Nature chemical biology · 2024Article
- Navigating Antibacterial Frontiers: A Panoramic Exploration of Antibacterial Landscapes, Resistance Mechanisms, and Emerging Therapeutic Strategies.ACS infectious diseases · 2024Review
- Using permeation guidelines to design new antibiotics-A PASsagE into Pseudomonas aeruginosa.Clinical and translational medicine · 2024Article
- Engineered and total biosynthesis of fungal specialized metabolites.Nature reviews. Chemistry · 2024Review
- Article
- Strategies to access the [5-8] bicyclic core encountered in the sesquiterpene, diterpene and sesterterpene series.Beilstein journal of organic chemistry · 2023Review
Corrections and comments
- Erratum issued
Authors and funding
3 authors.
Funding
Abstract
The emergence of drug-resistant bacterial pathogens has placed renewed emphasis on the total chemical synthesis of novel antibacterials. Tetracyclines, macrolides, streptogramins and lincosamides are now accessible through flexible and general synthetic routes. Pleuromutilins (antibiotics based on the fungal metabolite pleuromutilin) have remained resistant to this approach, in large part due to the difficulties encountered in the de novo construction of the decahydro-3a,9-propanocyclopenta[8]annulene skeleton. Here we present a platform for the total synthesis of pleuromutilins that provides access to diverse derivatives bearing alterations at previously inaccessible skeletal and peripheral positions. The synthesis is enabled by the serendipitous discovery of a vinylogous Wolff rearrangement, which serves to establish the C9 quaternary centre in the targets, and the development of a highly diastereoselective butynylation of an α-quaternary aldehyde, which forms the C14 secondary alcohol. The versatility of the route is demonstrated through the synthesis of seventeen structurally distinct derivatives, with many possessing potent antibacterial activity.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.