Evidence map›Paper›PMID 37730908›Full record

ReviewNature reviews. Chemistry2023

Strategic application of C-H oxidation in natural product total synthesis.

Ian Bakanas, Robert F Lusi, Stefan Wiesler, Jack Hayward Cooke, Richmond Sarpong

Abstract readReview
PubMed Publisher
In one paragraph

Review in Nature reviews. Chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.

0numbers the graph read from it
0cells of the map it votes in
19citing 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

19 citing papers in PubMed.

  1. Article
  2. Article
  3. Review
  4. Article
  5. Article
  6. Article
  7. Review
  8. Article
  9. Review
  10. Late-Stage Oxidation of C(spAngewandte Chemie (International ed. in English) · 2025
    Article
  11. Review
  12. Total Synthesis of the Nominal Structure of (+)-Talaromyolide D.Journal of the American Chemical Society · 2025
    Article
  13. Article
  14. Article
  15. Advancing Total Synthesis Through Skeletal Editing.Accounts of chemical research · 2025
    Article
  16. Hydrogen Atom Transfer-Based C(spThe Journal of organic chemistry · 2025
    Article
  17. Article
  18. Switchable Site-Selective Benzanilide C(spMolecules (Basel, Switzerland) · 2024
    Article
  19. Progress in Lewis-Acid-Templated Diels-Alder Reactions.Molecules (Basel, Switzerland) · 2024
    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

5 authors.

Ian Bakanas *Department of Chemistry, University of California, Berkeley, Berkeley, CA, USA.
Robert F Lusi *Department of Chemistry, University of California, Berkeley, Berkeley, CA, USA.ORCID http://orcid.org/0000-0002-4627-3229
Stefan WieslerDepartment of Chemistry, University of California, Berkeley, Berkeley, CA, USA.ORCID http://orcid.org/0000-0002-4302-7639
Jack Hayward CookeDepartment of Chemistry, University of California, Berkeley, Berkeley, CA, USA.ORCID http://orcid.org/0000-0002-9810-0610
Richmond SarpongDepartment of Chemistry, University of California, Berkeley, Berkeley, CA, USA. rsarpong@berkeley.edu.ORCID http://orcid.org/0000-0002-0028-6323

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

The oxidation of unactivated C-H bonds has emerged as an effective tactic in natural product synthesis and has altered how chemists approach the synthesis of complex molecules. The use of C-H oxidation methods has simplified the process of synthesis planning by expanding the choice of starting materials, limiting functional group interconversion and protecting group manipulations, and enabling late-stage diversification. In this Review, we propose classifications for C-H oxidations on the basis of their strategic purpose: type 1, which installs functionality that is used to establish the carbon skeleton of the target; type 2, which is used to construct a heterocyclic ring; and type 3, which installs peripheral functional groups. The reactions are further divided based on whether they are directed or undirected. For each classification, examples from recent literature are analysed. Finally, we provide two case studies of syntheses from our laboratory that were streamlined by the judicious use of C-H oxidation reactions.

Identifiers

PMID37730908

What Socratic holds

Textmetadata
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 Socratic graph.