Evidence map›Paper›PMID 33682403›Full record

ArticleJournal of the American Chemical Society2021

Taming Radical Pairs in the Crystalline Solid State: Discovery and Total Synthesis of Psychotriadine.

Jordan J Dotson, Ieva Liepuoniute, J Logan Bachman, Vince M Hipwell, Saeed I Khan, K N Houk, Neil K Garg, Miguel A Garcia-Garibay

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.

0numbers the graph read from it
0cells of the map it votes in
11citing 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

11 citing papers in PubMed.

  1. Skeletal Reorganization of Cycloalkylamines Into Angular Azatetracyclic Scaffolds.Angewandte Chemie (International ed. in English) · 2026
    Article
  2. Article
  3. Review
  4. Article
  5. Unified Total Synthesis ofJournal of the American Chemical Society · 2025
    Article
  6. Review
  7. Article
  8. Article
  9. Article
  10. Article
  11. 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.

Jordan J DotsonDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.
Ieva LiepuoniuteDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.ORCID 0000-0003-2965-8642
J Logan BachmanDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.
Vince M HipwellDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.
Saeed I KhanDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.
K N HoukDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.ORCID 0000-0002-8387-5261
Neil K GargDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.ORCID 0000-0002-7793-2629
Miguel A Garcia-GaribayDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.ORCID 0000-0002-6268-1943

Funding

Time-of-Flight Mass Spectrometer for Synthesis Supporting Biomedical ResearchS10RR025631 · NCRR · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI HOUK, KENDALL N · 2009 to 2009
$328k
NCRR NIH HHS S10 RR025631
6 · The paper itself

Abstract

Solid-state photodecarbonylation is an attractive but underutilized methodology to forge hindered C-C bonds in complex molecules. This study discloses the use of this reaction to assemble the vicinal quaternary stereocenter motif present in bis(cyclotryptamine) alkaloids. Our strategy was enabled by experimental and computational investigations of the role of substrate conformation on the success or failure of the solid-state photodecarbonylation reaction. This informed a crystal engineering strategy to optimize the key step of the total synthesis. Ultimately, this endeavor culminated in the successful synthesis of the bis(cyclotryptamine) alkaloid "psychotriadine," which features the elusive piperidinoindoline framework. Psychotriadine, a previously unknown compound, was identified in the extracts of the flower

Indexed as

AlkaloidsCarbonFree RadicalsIndolesLightMolecular ConformationPiperidinesStereoisomerismAlkaloidsCarbonFree RadicalsIndolesindolinepiperidinePiperidines

Identifiers

PMID33682403
PMCPMC8292139

What OpenQuestion holds

Textmetadata
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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.