Evidence map›Paper›PMID 37877778›Full record

ArticleAngewandte Chemie (International ed. in English)2023

Stereospecific Conversion of Boronic Esters into Enones using Methoxyallene: Application in the Total Synthesis of 10-Deoxymethynolide.

Kristian J Chambers, Patthadon Sanghong, Daniel Carter Martos, Giorgia Casoni, Rory C Mykura, Durga Prasad Hari, Adam Noble, Varinder K Aggarwal

Open access · hybridAbstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.

0numbers the graph read from it
0cells of the map it votes in
3citing papers in PubMed
2.1field-weighted citation impact, top 13% of its field
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

3 citing papers in PubMed, 14 citations in OpenAlex.

  1. Eschenmoser's salts: from design to applications in organic synthesis.Organic chemistry frontiers : an international journal of organic chemistry · 2026
    Review
  2. Review
  3. 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

8 authors at 1 institution in 1 country.

Kristian J ChambersSchool of Chemistry, University of Bristol, Cantock's Close, BS8 1TS, Bristol, UK.
Patthadon SanghongSchool of Chemistry, University of Bristol, Cantock's Close, BS8 1TS, Bristol, UK.
Daniel Carter MartosSchool of Chemistry, University of Bristol, Cantock's Close, BS8 1TS, Bristol, UK.ORCID https://orcid.org/0000-0003-4441-4427
Giorgia CasoniSchool of Chemistry, University of Bristol, Cantock's Close, BS8 1TS, Bristol, UK.
Rory C MykuraSchool of Chemistry, University of Bristol, Cantock's Close, BS8 1TS, Bristol, UK.
Durga Prasad HariSchool of Chemistry, University of Bristol, Cantock's Close, BS8 1TS, Bristol, UK.
Adam NobleSchool of Chemistry, University of Bristol, Cantock's Close, BS8 1TS, Bristol, UK.ORCID https://orcid.org/0000-0001-9203-7828
Varinder K AggarwalSchool of Chemistry, University of Bristol, Cantock's Close, BS8 1TS, Bristol, UK.ORCID https://orcid.org/0000-0003-0344-6430
University of Bristol · GB

Funding

Engineering and Physical Sciences Research Council EP/L015366/1Engineering and Physical Sciences Research Council EP/T517872/1
6 · The paper itself

Abstract

Enones are widely utilized linchpin functional groups in chemical synthesis and molecular biology. We herein report the direct conversion of boronic esters into enones using commercially available methoxyallene as a three-carbon building block. Following boronate complex formation by reaction of the boronic ester with lithiated-methoxyallene, protonation triggers a stereospecific 1,2-migration before oxidation generates the enone. The protocol shows broad substrate scope and complete enantiospecificity is observed with chiral migrating groups. In addition, various electrophiles could be used to induce 1,2-migration and give a much broader range of α-functionalized enones. Finally, the methodology was applied to a 14-step synthesis of the enone-containing polyketide 10-deoxymethynolide.

Indexed as

EnonesLithiation-BorylationOrganoboron CompoundsStereospecificityTotal Synthesis

Identifiers

PMID37877778
PMCPMC10953306
OpenAlexW4387931803

What OpenQuestion holds

Textmetadata
LicenceCC BY
Read underepoch 390

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.