Evidence map›Paper›PMID 40728123›Full record

ArticleThe Journal of organic chemistry2025

Annulation Methods toward the Total Synthesis of Thermorubin: Construction of the AB and BCD Ring Systems.

Zachary A Kohanov, Andrew N Lowell

Abstract read
In one paragraph

Article in The Journal of organic chemistry, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it
0cells of the map it votes in
1citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

1 citing paper in PubMed.

  1. Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

2 authors.

Zachary A KohanovDepartment of Chemistry, Virginia Polytechnic Institute and State University (Virginia Tech), Blacksburg, Virginia 24061, United States.
Andrew N LowellDepartment of Chemistry, Virginia Polytechnic Institute and State University (Virginia Tech), Blacksburg, Virginia 24061, United States.ORCID 0000-0001-5357-5279

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

New antibiotics are desperately needed to fight the growing threat of antimicrobial resistance. Thermorubin, a forgotten natural product, is one such candidate, as it binds to a novel site on the ribosome and uniquely disrupts both elongation and termination during protein synthesis. In this study, we report the synthesis of the AB and BCD ring portions of thermorubin in a 10% yield over six steps and an 8.9% yield over seven steps, respectively. The key disconnection for both systems involved identification of a symmetric nucleophilic donor synthon suitable for annulation with Michael acceptors within the core tetracycle─an unusual planar aromatic system. An activated form of this symmetric intermediate enabled a formal [4 + 2] cycloaddition with a 6-carboxy pyrone as well as traditional α-β-unsaturated ketones. Beyond advancing the total synthesis of thermorubin, these strategies offer broader utility for the construction of other complex heterocycles.

Indexed as

Anti-Bacterial AgentsCycloaddition ReactionKetonesMolecular StructureAnti-Bacterial AgentsKetones

Identifiers

PMID40728123
PMCPMC12340950

What OpenQuestion holds

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LicenceCC BY
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Registered trials

None linked

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.