Evidence map›Paper›PMID 37387644›Full record

ArticleOrganic letters2023

Cyclic Allene Approach to the Manzamine Alkaloid Keramaphidin B.

Milauni M Mehta, Jordan A M Gonzalez, James L Bachman, Neil K Garg

Abstract read
In one paragraph

Article in Organic letters, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.

0numbers the graph read from it
0cells of the map it votes in
7citing 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

7 citing papers in PubMed.

  1. Article
  2. Article
  3. Total Synthesis of Lissodendoric Acid A.Angewandte Chemie (International ed. in English) · 2024
    Article
  4. Article
  5. Article
  6. Article
  7. Total Synthesis of Njaoamine C by Concurrent Macrocycle Formation.Journal of the American Chemical Society · 2023
    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.

Milauni M MehtaDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States.ORCID 0000-0002-4597-2829
Jordan A M GonzalezDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States.ORCID 0000-0003-0165-6311
James L BachmanDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States.
Neil K GargDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States.ORCID 0000-0002-7793-2629

Funding

Exploiting Unconventional Building Blocks in Chemical SynthesisR35GM139593 · NIGMS · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI Neil K. Garg · 2021 to 2026
$4.0M
Chemistry Biology Interface Training ProgramT32GM136614 · NIGMS · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI Patrick G. Harran · 2020 to 2026
$2.8M
Time-of-Flight Mass Spectrometer for Synthesis Supporting Biomedical ResearchS10RR025631 · NCRR · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI HOUK, KENDALL N · 2009 to 2009
$328k
Total Synthesis of Keramaphidin B via an Azacyclic Allene IntermediateF32GM136171 · NIGMS · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI BACHMAN, JAMES L · 2020 to 2021
$84k
NCRR NIH HHS S10 RR025631NIGMS NIH HHS F32 GM136171NIGMS NIH HHS R35 GM139593NIGMS NIH HHS T32 GM136614
6 · The paper itself

Abstract

We report an approach to the core of the manzamine alkaloid keramaphidin B that relies on the strain-promoted cycloaddition of an azacyclic allene with a pyrone trapping partner. The cycloaddition is tolerant of nitrile and primary amide functional groups and can be complemented with a subsequent retro-Diels-Alder step. These efforts demonstrate that strained cyclic allenes can be used to build significant structural complexity and should encourage further studies of these fleeting intermediates.

Indexed as

AlkadienesAlkaloidsCycloaddition ReactionNitrilesPyridinesAlkadienesAlkaloidskeramaphidin BNitrilespropadienePyridines

Identifiers

PMID37387644
PMCPMC10460088

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.