Evidence map›Paper›PMID 36739571›Full record

ArticleOrganic letters2023

Development of α-Selective Glycosylation with l-Oleandral and Its Application to the Total Synthesis of Oleandrin.

Nolan Carney, Natasha Perry, Jacob Garabedian, Pavel Nagorny

Open access · greenAbstract read
In one paragraph

Article in Organic letters, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.

0numbers the graph read from it
0cells of the map it votes in
9citing papers in PubMed
2.4field-weighted citation impact, top 12% 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

9 citing papers in PubMed, 16 citations in OpenAlex.

  1. Article
  2. Article
  3. Review
  4. Article
  5. Digoxin and its NaBioorganic & medicinal chemistry · 2024
    Review
  6. Article
  7. Article
  8. Article
  9. 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

4 authors at 1 institution in 1 country.

Nolan CarneyProgram in Chemical Biology, University of Michigan, Ann Arbor, Michigan 48109, United States.
Natasha PerryDepartment of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States.
Jacob GarabedianDepartment of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States.
Pavel NagornyDepartment of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States.ORCID 0000-0002-7043-984X
University of Michigan · US

Funding

New Methods and Strategies for the Synthesis and Selective Derivatization of Natural ProductsR35GM136341 · NIGMS · UNIVERSITY OF MICHIGAN AT ANN ARBOR · PI Pavel Nagorny · 2020 to 2026
$2.6M
NIGMS NIH HHS R35 GM136341
6 · The paper itself

Abstract

This letter describes the development of an α-selective glycosylation using l-oleandrose, a 2-deoxysugar that is frequently found in natural products, and its application to the total synthesis of the natural cardiotonic steroids oleandrin and beaumontoside. To improve the reaction diastereoselectivity and to minimize side-product formation, an extensive evaluation and optimization of the conditions leading to α-selective glycosylation of digitoxigenin with l-oleandrose-based donors was conducted. These studies led to the exploration of 8 different phosphine·acid complexes or salts and yielded HBr·PPh

Indexed as

Cardiac GlycosidesCardenolidesDigitoxigeninGlycosylationCardenolidesCardiac GlycosidesDigitoxigeninoleandrin

Identifiers

PMID36739571
PMCPMC10278664
OpenAlexW4319241304

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.