Synthesis of Thienamycin methyl ester from 2-deoxy-D-ribose via Kinugasa reaction.

Magdalena Soluch, Barbara Grzeszczyk, Olga Staszewska-Krajewska, Marek Chmielewski, Bartłomiej Furman

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Article in The Journal of antibiotics, 2016. 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

1.7field-weighted citation impact, top 16% 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

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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, 12 citations in OpenAlex.

Formal synthesis of Thienamycin.The Journal of antibiotics · 2017
Article

4 · The record

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5 · Who and what money

Authors and funding

5 authors at 2 institutions in 1 country.

Magdalena SoluchInstitute of Organic Chemistry of Polish Academy of Sciences, Warsaw, Poland.

Barbara GrzeszczykInstitute of Organic Chemistry of Polish Academy of Sciences, Warsaw, Poland.

Olga Staszewska-KrajewskaInstitute of Organic Chemistry of Polish Academy of Sciences, Warsaw, Poland.

Marek ChmielewskiInstitute of Organic Chemistry of Polish Academy of Sciences, Warsaw, Poland.

Bartłomiej FurmanInstitute of Organic Chemistry of Polish Academy of Sciences, Warsaw, Poland.

Institute of Organic Chemistry · PLPolish Academy of Sciences · PL

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

A novel synthesis of thienamycin is described. The crucial step of the synthesis is based on Cu(I)-mediated Kinugasa cycloaddition/rearrangement cascade reaction between terminal acetylene derived from D-lactic acid and suitable, partially protected, five-membered cyclic nitrone obtained from 2-deoxy-D-ribose. The reaction was performed in the presence of tetramethylguanidine as a base to provide 5,6-trans substituted carbapenam as the main product. Thus obtained carbapenam 11 with (5R,6S) configuration at the azetidinone ring was subsequently subjected to oxidation/deprotection/oxidation reaction sequence to afford the β-keto ester 20, which was directly transformed into N,O-protected methyl ester of thienamycin.

Indexed as

AzetidinesDeoxyriboseLactic AcidMolecular StructureNitrogen OxidesOxidation-ReductionThienamycins2-azetidinoneAzetidinesDeoxyriboseLactic AcidNitrogen OxidesnitronesthienamycinThienamycins

Identifiers

PMID26506859

DOI10.1038/ja.2015.108

OpenAlexW2255704001

What OpenQuestion holds

Textmetadata

Read underepoch 390

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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.