Evidence map›Paper›PMID 30573544›Full record

ArticleScience (New York, N.Y.)2019

Concise total syntheses of (-)-jorunnamycin A and (-)-jorumycin enabled by asymmetric catalysis.

Eric R Welin, Aurapat Ngamnithiporn, Max Klatte, Guillaume Lapointe, Gerit M Pototschnig, Martina S J McDermott, Dylan Conklin, Christopher D Gilmore, Pamela M Tadross, Christopher K Haley and 7 more

Abstract read
In one paragraph

Article in Science (New York, N.Y.), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 32 papers.

0numbers the graph read from it
0cells of the map it votes in
32citing 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

32 citing papers in PubMed.

  1. Review
  2. Review
  3. Article
  4. Article
  5. Article
  6. Azine Dearomatization in Natural Product Total Synthesis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025
    Review
  7. Article
  8. Comparative analysis of complanadine A total syntheses.Beilstein journal of organic chemistry · 2025
    Review
  9. Article
  10. The Versatile and StrategicChemical reviews · 2024
    Review
  11. Article
  12. Article
  13. Review
  14. Review
  15. Review
  16. Article
  17. Article
  18. Article
  19. Iridium-catalyzed asymmetricChemical science · 2022
    Article
  20. 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

17 authors.

Eric R WelinWarren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA.ORCID 0000-0002-1760-4121
Aurapat NgamnithipornWarren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA.ORCID 0000-0002-5389-8171
Max KlatteWarren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA.
Guillaume LapointeWarren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA.
Gerit M PototschnigWarren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA.
Martina S J McDermottDivision of Hematology/Oncology, Department of Medicine, Geffen School of Medicine at UCLA, Los Angeles, CA, USA.
Dylan ConklinDivision of Hematology/Oncology, Department of Medicine, Geffen School of Medicine at UCLA, Los Angeles, CA, USA.ORCID 0000-0003-4708-0071
Christopher D GilmoreWarren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA.
Pamela M TadrossWarren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA.
Christopher K HaleyWarren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA.
Kenji NegoroWarren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA.ORCID 0000-0002-8341-5089
Emil GlibstrupWarren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA.ORCID 0000-0002-9060-6270
Christian U GrünangerWarren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA.
Kevin M AllanWarren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA.ORCID 0000-0002-7750-3621
Scott C VirgilWarren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA.ORCID 0000-0001-8586-5641
Dennis J SlamonDivision of Hematology/Oncology, Department of Medicine, Geffen School of Medicine at UCLA, Los Angeles, CA, USA. dslamon@mednet.ucla.edu stoltz@caltech.edu.ORCID 0000-0002-6330-498X
Brian M StoltzWarren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA. dslamon@mednet.ucla.edu stoltz@caltech.edu.ORCID 0000-0001-9837-1528

Funding

Synthesis of Bioactive Bis-Tetrahydroisoquinoline AlkaloidsR01GM127972 · NIGMS · CALIFORNIA INSTITUTE OF TECHNOLOGY · PI STOLTZ, BRIAN M · 2018 to 2021
$1.2M
Austrian Science Fund FWF J 3893NIGMS NIH HHS R01 GM127972
6 · The paper itself

Abstract

The bis-tetrahydroisoquinoline (bis-THIQ) natural products have been studied intensively over the past four decades for their exceptionally potent anticancer activity, in addition to strong Gram-positive and Gram-negative antibiotic character. Synthetic strategies toward these complex polycyclic compounds have relied heavily on electrophilic aromatic chemistry, such as the Pictet-Spengler reaction, that mimics their biosynthetic pathways. Herein, we report an approach to two bis-THIQ natural products, jorunnamycin A and jorumycin, that instead harnesses the power of modern transition-metal catalysis for the three major bond-forming events and proceeds with high efficiency (15 and 16 steps, respectively). By breaking from biomimicry, this strategy allows for the preparation of a more diverse set of nonnatural analogs.

Indexed as

Antineoplastic AgentsCatalysisCell Line, TumorDrug DiscoveryHumansHydrogenationIsoquinolinesMolecular StructureQuinolonesTetrahydroisoquinolinesAntineoplastic AgentsIsoquinolinesjorumycinjorunnamycin AQuinolonesTetrahydroisoquinolines

Identifiers

PMID30573544
PMCPMC7017906

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.