Evidence map›Paper›PMID 31276621›Full record

ArticleJournal of the American Chemical Society2019

Total Synthesis of the Diterpenoid Alkaloid Arcutinidine Using a Strategy Inspired by Chemical Network Analysis.

Kyle R Owens, Shelby V McCowen, Katherine A Blackford, Sohei Ueno, Yasuo Hirooka, Manuel Weber, Richmond Sarpong

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.

0numbers the graph read from it
0cells of the map it votes in
10citing 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

10 citing papers in PubMed.

  1. Article
  2. Article
  3. Entry Steps in the Biosynthetic Pathway to Diterpenoid Alkaloids inbioRxiv : the preprint server for biology · 2025
    Article
  4. Article
  5. Navigating Excess Complexity: Total Synthesis of Daphenylline.Journal of the American Chemical Society · 2024
    Article
  6. Review
  7. Review
  8. Fe-Catalyzed Anaerobic Mukaiyama-Type Hydration of Alkenes using Nitroarenes.Angewandte Chemie (International ed. in English) · 2021
    Article
  9. Article
  10. 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

7 authors.

Kyle R OwensDepartment of Chemistry , University of California , Berkeley , California 94720 , United States.
Shelby V McCowenDepartment of Chemistry , University of California , Berkeley , California 94720 , United States.
Katherine A BlackfordDepartment of Chemistry , University of California , Berkeley , California 94720 , United States.
Sohei UenoDepartment of Chemistry , University of California , Berkeley , California 94720 , United States.
Yasuo HirookaDepartment of Chemistry , University of California , Berkeley , California 94720 , United States.
Manuel WeberDepartment of Chemistry , University of California , Berkeley , California 94720 , United States.
Richmond SarpongDepartment of Chemistry , University of California , Berkeley , California 94720 , United States.ORCID 0000-0002-0028-6323

Funding

Strategies and Methods for Complex Molecule Synthesis: Acquisition of a 400 MHz Nuclear Magnetic Resonance Spectrometer ConsoleR35GM130345 · NIGMS · UNIVERSITY OF CALIFORNIA BERKELEY · PI Richmond Sarpong · 2019 to 2026
$5.4M
High Performance Computing Cluster for Public Health Driven Molecular Science - Core FacilityS10OD023532 · OD · UNIVERSITY OF CALIFORNIA BERKELEY · PI DURKIN, KATHLEEN A · 2017 to 2017
$434k
NIGMS NIH HHS R35 GM130345NIH HHS S10 OD023532
6 · The paper itself

Abstract

Arcutinidine and other arcutinidine-type diterpenoid alkaloids feature an intricate polycyclic, bridged framework with unusual connectivity. A chemical network analysis approach to the arcutane skeleton enabled the identification of highly simplifying retrosynthetic disconnections, which indicated that the caged structure could arise from a simpler fused ring system. On this basis, a total synthesis of arcutinidine is reported herein, featuring an unprecedented oxopyrrolium Diels-Alder cycloaddition which furnishes a key tetracyclic intermediate. In addition, the synthesis utilizes a diastereoselective oxidative dearomatization/cycloaddition sequence and a SmI

Indexed as

Biological ProductsCycloaddition ReactionMolecular StructureBiological Products

Identifiers

PMID31276621
PMCPMC7771644

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.