Evidence map›Paper›PMID 27556024›Full record

ArticleFrontiers in chemistry2016

Total Synthesis of Putative 11-epi-Lyngbouilloside Aglycon.

Amandine Kolleth, Julian Gebauer, Abdelatif ElMarrouni, Raphael Lebeuf, Céline Prévost, Eric Brohan, Stellios Arseniyadis, Janine Cossy

Abstract read
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In one paragraph

Article in Frontiers in chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing 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

2 citing papers in PubMed.

  1. Article
  2. 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

8 authors.

Amandine KollethLaboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation, ESPCI Paris, Centre National de la Recherche Scientifique (UMR8231), PSL Research University Paris, France.
Julian GebauerLaboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation, ESPCI Paris, Centre National de la Recherche Scientifique (UMR8231), PSL Research University Paris, France.
Abdelatif ElMarrouniLaboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation, ESPCI Paris, Centre National de la Recherche Scientifique (UMR8231), PSL Research University Paris, France.
Raphael LebeufLaboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation, ESPCI Paris, Centre National de la Recherche Scientifique (UMR8231), PSL Research University Paris, France.
Céline PrévostLGCR-Analytical Sciences, Sanofi Vitry-sur-Seine, France.
Eric BrohanLGCR-Analytical Sciences, Sanofi Vitry-sur-Seine, France.
Stellios ArseniyadisLaboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation, ESPCI Paris, Centre National de la Recherche Scientifique (UMR8231), PSL Research University Paris, France.
Janine CossyLaboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation, ESPCI Paris, Centre National de la Recherche Scientifique (UMR8231), PSL Research University Paris, France.

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

We report here the total synthesis of 11-epi-lyngbouilloside aglycon. Our strategy features a Boeckman-type esterification followed by a RCM to form the 14-membered ring macrolactone and a late-stage side chain introduction via a Wittig olefination. Overall, the final product was obtained in 20 steps and 2% overall yield starting from commercially available 3-methyl-but-3-enol. Most importantly, the strategy employed is versatile enough to eventually allow us to complete the synthesis of the natural product and irrevocably confirm its structure.

Indexed as

asymmetric Sharpless dihydroxylationBoeckman esterificationlyngbouillosideLyngbya bouilloniiMukaiyama aldolring-closing metathesistotal synthesis

Identifiers

PMID27556024
PMCPMC4977289

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.