Evidence map›Paper›PMID 30996125›Full record

ArticleProceedings of the National Academy of Sciences of the United States of America2019

Modular, stereocontrolled C

Ming Shang, Karla S Feu, Julien C Vantourout, Lisa M Barton, Heather L Osswald, Nobutaka Kato, Kerstin Gagaring, Case W McNamara, Gang Chen, Liang Hu and 9 more

Open access · hybridAbstract read
In one paragraph

Article in Proceedings of the National Academy of Sciences of the United States of America, 2019. 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
3.8field-weighted citation impact, top 6% 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

14 citing papers in PubMed, 52 citations in OpenAlex.

  1. Article
  2. Article
  3. Article
  4. Molecules (Basel, Switzerland) · 2025
    Article
  5. Article
  6. Vicinal stereocentersChemical science · 2023
    Article
  7. Article
  8. Review
  9. Article
  10. Article
  11. Ligand-Enabled β-Methylene C(spAngewandte Chemie (International ed. in English) · 2020
    Article
  12. Article
  13. Article
  14. 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

19 authors at 2 institutions in 1 country.

Ming ShangDepartment of Chemistry, The Scripps Research Institute, La Jolla, CA 92037.
Karla S FeuDepartment of Chemistry, The Scripps Research Institute, La Jolla, CA 92037.
Julien C VantouroutDepartment of Chemistry, The Scripps Research Institute, La Jolla, CA 92037.
Lisa M BartonDepartment of Chemistry, The Scripps Research Institute, La Jolla, CA 92037.
Heather L OsswaldDepartment of Chemistry, The Scripps Research Institute, La Jolla, CA 92037.
Nobutaka KatoChemical Biology and Therapeutics Science Program, Broad Institute, Cambridge, MA 02142.
Kerstin GagaringBiology Department, Calibr at The Scripps Research Institute, La Jolla, CA 92037.
Case W McNamaraBiology Department, Calibr at The Scripps Research Institute, La Jolla, CA 92037.
Gang ChenDepartment of Chemistry, The Scripps Research Institute, La Jolla, CA 92037.
Liang HuDepartment of Chemistry, The Scripps Research Institute, La Jolla, CA 92037.
Shengyang NiDepartment of Chemistry, The Scripps Research Institute, La Jolla, CA 92037.
Paula Fernández-CanelasDepartment of Chemistry, The Scripps Research Institute, La Jolla, CA 92037.
Miao ChenDepartment of Chemistry, The Scripps Research Institute, La Jolla, CA 92037.
Rohan R MerchantDepartment of Chemistry, The Scripps Research Institute, La Jolla, CA 92037.
Tian QinDepartment of Chemistry, The Scripps Research Institute, La Jolla, CA 92037.
Stuart L SchreiberChemical Biology and Therapeutics Science Program, Broad Institute, Cambridge, MA 02142.
Bruno MelilloDepartment of Chemistry, The Scripps Research Institute, La Jolla, CA 92037; bmelillo@scripps.edu yu200@scripps.edu pbaran@scripps.edu.
Jin-Quan YuDepartment of Chemistry, The Scripps Research Institute, La Jolla, CA 92037; bmelillo@scripps.edu yu200@scripps.edu pbaran@scripps.edu.
Phil S BaranDepartment of Chemistry, The Scripps Research Institute, La Jolla, CA 92037; bmelillo@scripps.edu yu200@scripps.edu pbaran@scripps.edu.ORCID 0000-0001-9193-9053
Scripps Research Institute · USBroad Institute · US

Funding

Scalable Synthesis and New Bond DisconnectionsR35GM118176 · NIGMS · SCRIPPS RESEARCH INSTITUTE, THE · PI BARAN, PHIL S · 2016 to 2025
$11.5M
NIGMS NIH HHS R35 GM118176
6 · The paper itself

Abstract

The union of two powerful transformations, directed C-H activation and decarboxylative cross-coupling, for the enantioselective synthesis of vicinally functionalized alkyl, carbocyclic, and heterocyclic compounds is described. Starting from simple carboxylic acid building blocks, this modular sequence exploits the residual directing group to access more than 50 scaffolds that would be otherwise extremely difficult to prepare. The tactical use of these two transformations accomplishes a formal vicinal difunctionalization of carbon centers in a way that is modular and thus, amenable to rapid diversity incorporation. A simplification of routes to known preclinical drug candidates is presented along with the rapid diversification of an antimalarial compound series.

Indexed as

carboxylic acidsC–H activationdecarboxylative cross-couplingmodularstereocontrolled

Identifiers

PMID30996125
PMCPMC6500144
OpenAlexW2937850742

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.