Evidence map›Paper›PMID 37691879›Full record

ArticleSynthesis2023

Synthesis of Guaipyridine Alkaloids Rupestine M and L by Cycloaddition/Cycloreversion of an Intermediate 1,4-Oxazinone.

Jonathan R Scheerer, Ella B Leeth, Jennifer A Sprow

Abstract read
In one paragraph

Article in Synthesis, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.

0numbers the graph read from it
0cells of the map it votes in
4citing 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

4 citing papers in PubMed.

  1. Article
  2. Article
  3. Polysubstituted Pyridines from 1,4-Oxazinone Precursors.The Journal of organic chemistry · 2024
    Article
  4. 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.

Jonathan R ScheererDepartment of Chemistry, William & Mary, P.O. Box 8795, Williamsburg, VA 23187, USA.
Ella B LeethDepartment of Chemistry, William & Mary, P.O. Box 8795, Williamsburg, VA 23187, USA.
Jennifer A SprowDepartment of Chemistry, William & Mary, P.O. Box 8795, Williamsburg, VA 23187, USA.

Funding

New methods to prepare 1,4-oxazin-2-ones and applications in the construction of polysubstituted pyridinesR15GM107702 · NIGMS · COLLEGE OF WILLIAM AND MARY · PI SCHEERER, JONATHAN R · 2014 to 2023
$987k
NIGMS NIH HHS R15 GM107702
6 · The paper itself

Abstract

A new method to prepare 1,4-oxazinone intermediates was developed based on aza-conjugate addition of β-amino alcohols to electron-deficient alkyne precursors. A tandem intramolecular cycloaddition/cycloreversion reaction sequence was evaluated, leading to the synthesis of the guaipyridine alkaloid natural products rupestine M and L. Starting from (-)-citronellal and thus a known configuration of the C5 stereocenter, a revised absolute configuration of natural rupestine L is suggested based on optical rotation.

Indexed as

1,4-oxazinonescycloadditioncycloreversionDiels–Alder reactiondomino reactionnatural product synthesispyridine synthesis

Identifiers

PMID37691879
PMCPMC10489027

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.