Evidence map›Paper›PMID 36538642›Full record

ArticleOrganic letters2022

Application of Lithiation-Borylation to the Total Synthesis of (-)-Rakicidin F.

Christian P Bold, Kay Yeung, Felix Pape, Daniel Kaiser, Varinder K Aggarwal

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Organic letters, 2022. 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. Review
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

5 authors.

Christian P BoldSchool of Chemistry, University of Bristol, Bristol BS8 1TS, U.K.ORCID 0000-0003-3810-8407
Kay YeungSchool of Chemistry, University of Bristol, Bristol BS8 1TS, U.K.
Felix PapeSchool of Chemistry, University of Bristol, Bristol BS8 1TS, U.K.
Daniel KaiserSchool of Chemistry, University of Bristol, Bristol BS8 1TS, U.K.ORCID 0000-0001-8895-9969
Varinder K AggarwalSchool of Chemistry, University of Bristol, Bristol BS8 1TS, U.K.ORCID 0000-0003-0344-6430

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

The stereochemistry of the lipophilic side chain of (+)-rakicidin F had not been determined until recently. Using our lithiation-borylation methodology ("assembly line synthesis") we were able to efficiently prepare the all-syn isomer as well as the C-21 epimer of the side chain, and comparison with the natural product suggested that the natural product had all-syn stereochemistry. Completion of the total synthesis using a macrolactamization of the northern amide enabled us to confirm Wang and Chen's stereochemical findings for the structure of (+)-rakicidin F.

Indexed as

Biological ProductsDepsipeptidesLipopeptidesMolecular StructureStereoisomerismBiological ProductsDepsipeptidesLipopeptidesrakicidins

Identifiers

PMID36538642
PMCPMC9806854

What OpenQuestion holds

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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.