Evidence map›Paper›PMID 26394844›Full record

ArticleJournal of the American Chemical Society2015

Highly Selective Synthesis of Halomon, Plocamenone, and Isoplocamenone.

Cyril Bucher, Richard M Deans, Noah Z Burns

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.

0numbers the graph read from it
0cells of the map it votes in
28citing 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

28 citing papers in PubMed.

  1. Eschenmoser's salts: from design to applications in organic synthesis.Organic chemistry frontiers : an international journal of organic chemistry · 2026
    Review
  2. Review
  3. Article
  4. Article
  5. Article
  6. Article
  7. Article
  8. Naturally Occurring Organohalogen Compounds-A Comprehensive Review.Progress in the chemistry of organic natural products · 2023
    Review
  9. Article
  10. The Electrochemical cis-Chlorination of Alkenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021
    Article
  11. Article
  12. Cross-Electrophile Coupling of Unactivated Alkyl Chlorides.Journal of the American Chemical Society · 2020
    Article
  13. Review
  14. Article
  15. Enantioselective Synthesis of Azamerone.Journal of the American Chemical Society · 2019
    Article
  16. Total Enzyme Syntheses of Napyradiomycins A1 and B1.Journal of the American Chemical Society · 2018
    Article
  17. Catalytic Regio- and Enantioselective Haloazidation of Allylic Alcohols.Journal of the American Chemical Society · 2018
    Article
  18. Review
  19. Review
  20. 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

3 authors.

Cyril BucherDepartment of Chemistry, Stanford University , Stanford, California 94305, United States.
Richard M DeansDepartment of Chemistry, Stanford University , Stanford, California 94305, United States.
Noah Z BurnsDepartment of Chemistry, Stanford University , Stanford, California 94305, United States.

Funding

Structure, Mechanism, and Engineering of Assembly Line Polyketide SynthasesR01GM087934 · NIGMS · STANFORD UNIVERSITY · PI KHOSLA, CHAITAN · 2009 to 2021
$4.9M
Selective Halogenation Reactions for the Synthesis of Chiral Bioactive Small MoleculesR01GM114061 · NIGMS · STANFORD UNIVERSITY · PI BURNS, NOAH ZACHARY · 2015 to 2019
$1.5M
NIGMS NIH HHS R01 GM087934NIGMS NIH HHS R01 GM114061
6 · The paper itself

Abstract

Over 160 chiral vicinal bromochlorinated natural products have been identified; however, a lack of synthetic methods for the selective incorporation of halogens into organic molecules has hindered their synthesis. Here we disclose the first total synthesis and structural confirmation of isoplocamenone and plocamenone, as well as the first selective and scalable synthesis of the preclinical anticancer natural product halomon. The synthesis of these inter-halogenated compounds has been enabled by our recently developed chemo-, regio-, and enantioselective dihalogenation reaction.

Indexed as

Biological ProductsHydrocarbons, Halogenated6-bromo-3-(bromomethyl)-7-methyl-2,3,7-trichloro-1-octeneBiological ProductsHydrocarbons, Halogenated

Identifiers

PMID26394844
PMCPMC4634703

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.