Evidence map›Paper›PMID 32338003›Full record

ArticleJournal of the American Chemical Society2020

Total Synthesis of (-)-Maximiscin.

Kyle S McClymont, Feng-Yuan Wang, Amin Minakar, Phil S Baran

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.

0numbers the graph read from it
0cells of the map it votes in
14citing 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

14 citing papers in PubMed.

  1. Article
  2. Article
  3. Review
  4. Review
  5. Article
  6. Review
  7. Article
  8. Article
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  11. Article
  12. Article
  13. Article
  14. Ideality in Context: Motivations for Total Synthesis.Accounts of chemical research · 2021
    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

4 authors.

Kyle S McClymontDepartment of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.ORCID 0000-0002-2806-9056
Feng-Yuan WangDepartment of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Amin MinakarDepartment of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Phil S BaranDepartment of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.ORCID 0000-0001-9193-9053

Funding

Scalable Synthesis and New Bond DisconnectionsR35GM118176 · NIGMS · SCRIPPS RESEARCH INSTITUTE, THE · PI BARAN, PHIL S · 2016 to 2025
$11.5M
Parallel Pressure Reactor with Sampling CapabilitiesS10OD025208 · OD · SCRIPPS RESEARCH INSTITUTE, THE · PI CHEN, JASON SHIH-HAO · 2018 to 2018
$591k
NIGMS NIH HHS R35 GM118176NIH HHS S10 OD025208
6 · The paper itself

Abstract

A short, enantioselective synthesis of (-)-maximiscin, a structurally intriguing metabolite of mixed biosynthetic origin, is reported. A retrosynthetic analysis predicated on maximizing ideality and efficiency led to several unusual disconnections and tactics. Formation of the central highly oxidized pyridone ring through a convergent coupling at the end of the synthesis simplified the route considerably. The requisite building blocks could be prepared from feedstock materials (derived from shikimate and mesitylene). Strategies rooted in hidden symmetry recognition, C-H functionalization, and radical retrosynthesis played key roles in developing this concise route.

Indexed as

Heterocyclic Compounds, 4 or More RingsMolecular ConformationStereoisomerismHeterocyclic Compounds, 4 or More Ringsmaximiscin

Identifiers

PMID32338003
PMCPMC8025790

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.