Evidence map›Paper›PMID 30566336›Full record

ArticleJournal of the American Chemical Society2019

Asymmetric Synthesis of Griffipavixanthone Employing a Chiral Phosphoric Acid-Catalyzed Cycloaddition.

Michael J Smith, Kyle D Reichl, Randolph A Escobar, Thomas J Heavey, David F Coker, Scott E Schaus, John A Porco

Open access · greenAbstract 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 3 papers.

0numbers the graph read from it
0cells of the map it votes in
3citing papers in PubMed
1.0field-weighted citation impact, top 26% 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

3 citing papers in PubMed, 20 citations in OpenAlex.

  1. Substrate- and Reagent-Controlled Dimerization of VinylThe Journal of organic chemistry · 2025
    Article
  2. Article
  3. Anti-Tumor Xanthones fromDrug design, development and therapy · 2020
    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

7 authors at 1 institution in 1 country.

Michael J SmithDepartment of Chemistry and Center for Molecular Discovery (BU-CMD) , Boston University , 590 Commonwealth Avenue , Boston , Massachusetts 02215 , United States.ORCID 0000-0002-0389-6864
Kyle D ReichlDepartment of Chemistry and Center for Molecular Discovery (BU-CMD) , Boston University , 590 Commonwealth Avenue , Boston , Massachusetts 02215 , United States.ORCID 0000-0001-7779-0846
Randolph A EscobarDepartment of Chemistry and Center for Molecular Discovery (BU-CMD) , Boston University , 590 Commonwealth Avenue , Boston , Massachusetts 02215 , United States.
Thomas J HeaveyDepartment of Chemistry and Center for Molecular Discovery (BU-CMD) , Boston University , 590 Commonwealth Avenue , Boston , Massachusetts 02215 , United States.
David F CokerDepartment of Chemistry and Center for Molecular Discovery (BU-CMD) , Boston University , 590 Commonwealth Avenue , Boston , Massachusetts 02215 , United States.ORCID 0000-0001-6210-5228
Scott E SchausDepartment of Chemistry and Center for Molecular Discovery (BU-CMD) , Boston University , 590 Commonwealth Avenue , Boston , Massachusetts 02215 , United States.ORCID 0000-0002-5877-6587
John A PorcoDepartment of Chemistry and Center for Molecular Discovery (BU-CMD) , Boston University , 590 Commonwealth Avenue , Boston , Massachusetts 02215 , United States.ORCID 0000-0002-2991-5680
Boston University · US

Funding

Chemical Synthesis of Complex Natural Products for Translational ScienceR35GM118173 · NIGMS · BOSTON UNIVERSITY (CHARLES RIVER CAMPUS) · PI JOHN A. PORCO · 2016 to 2026
$8.2M
The Design and Implementation of Asymmetric Organocatalysis in SynthesisR01GM078240 · NIGMS · BOSTON UNIVERSITY (CHARLES RIVER CAMPUS) · PI SCHAUS, SCOTT EDWARD · 2007 to 2018
$2.9M
Center for Molecular Discovery (CMD): A Small Molecule Resource for Biomedical ResearchR24GM111625 · NIGMS · BOSTON UNIVERSITY (CHARLES RIVER CAMPUS) · PI PORCO, JOHN A. · 2015 to 2017
$1.5M
NIGMS NIH HHS R01 GM078240NIGMS NIH HHS R24 GM111625NIGMS NIH HHS R35 GM118173
6 · The paper itself

Abstract

Asymmetric synthesis of the biologically active xanthone dimer griffipavixanthone is reported along with its absolute stereochemistry determination. Synthesis of the natural product is accomplished via dimerization of a p-quinone methide using a chiral phosphoric acid catalyst to afford a protected precursor in excellent diastereo- and enantioselectivity. Mechanistic studies, including an unbiased computational investigation of chiral ion-pairs using parallel tempering, were performed in order to probe the mode of asymmetric induction.

Indexed as

CatalysisChemistry Techniques, SyntheticModels, MolecularMolecular ConformationPhosphoric AcidsXanthonesphosphoric acidPhosphoric AcidsxanthoneXanthones

Identifiers

PMID30566336
PMCPMC6475489
OpenAlexW2905236298

What OpenQuestion holds

Textmetadata
LicenceTDM
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.