Synthesis of the ABC framework of tamulamides A and B.

Elizabeth H Kelley, Timothy F Jamison

Abstract read

In one paragraph

Article in Bioorganic & medicinal chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it

0cells of the map it votes in

1citing 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

1 citing paper in PubMed.

Experimental and Computational Studies on Regiodivergent Chiral Phosphoric Acid Catalyzed Cycloisomerization of Mupirocin Methyl Ester.Chemistry (Weinheim an der Bergstrasse, Germany) · 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

2 authors.

Elizabeth H KelleyDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave., Cambridge, MA 02139, United States.

Timothy F JamisonDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave., Cambridge, MA 02139, United States. Electronic address: tfj@mit.edu.

Funding

Synthetic Strategies based on expoxide coupling reactionsR01GM072566 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI JAMISON, TIMOTHY F · 2005 to 2017

$3.1M

NIGMS NIH HHS R01 GM072566

6 · The paper itself

Abstract

Synthesis of the fused tetrahydrofuran motif comprising the ABC rings of the marine ladder polyethers tamulamides A and B has been achieved via two different polyepoxide cascade strategies. Investigations into a triepoxide cascade under aqueous conditions revealed the importance of the electronic nature of the cascade end-group with this initial approach. Ultimately, a diepoxide cascade under basic conditions proved most successful, providing the ABC tetrahydropyran triad in 41% yield.

Indexed as

CyclizationEpoxy CompoundsFuransMarine ToxinsOxocinsEpoxy CompoundsFuransMarine ToxinsOxocinstamulamide Atamulamide BtetrahydrofuranCascade reactionsEpoxide openingsNatural productsOxygen heterocyclesPolyethers

Identifiers

PMID29729986

DOI10.1016/j.bmc.2018.04.046

PMCPMC6657502

What OpenQuestion holds

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Registered trials

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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.