Evidence map›Paper›PMID 38587582›Full record

ArticleJournal of natural medicines2024

Proposal for structure revision of pinofuranoxin A through total syntheses of stereoisomers.

Kazuki Ujiie, Chiaki Tanaka, Masayoshi Arai, Masaru Hashimoto, Yuki Yoshida, Tomikazu Kawano, Satoru Tamura

Abstract read
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Article in Journal of natural medicines, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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0citing papers in PubMed
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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

0 citing papers in PubMed.

No citing paper in PubMed yet.

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

7 authors.

Kazuki UjiieLaboratory of Natural Products Chemistry, School of Pharmaceutical Sciences, Wakayama Medical University, 25-1 Shichibancho, Wakayama, 640-8156, Japan.
Chiaki TanakaLaboratory of Natural Products Chemistry, School of Pharmaceutical Sciences, Wakayama Medical University, 25-1 Shichibancho, Wakayama, 640-8156, Japan.
Masayoshi AraiLaboratory of Natural Products for Drug Discovery, Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-Oka, Suita, Osaka, 565-0871, Japan.
Masaru HashimotoDepartment of Biochemistry and Molecular Biology, Faculty of Agriculture and Life Science, Hirosaki University, 3-Bunkyo-Cho, Hirosaki, 036-8561, Japan.
Yuki YoshidaDepartment of Medicinal and Organic Chemistry, School of Pharmacy, Iwate Medical University, 1-1-1 Idai-Dori, Yahaba-Cho, Shiwa-Gun, Iwate, 028-3694, Japan.
Tomikazu KawanoDepartment of Medicinal and Organic Chemistry, School of Pharmacy, Iwate Medical University, 1-1-1 Idai-Dori, Yahaba-Cho, Shiwa-Gun, Iwate, 028-3694, Japan.
Satoru TamuraLaboratory of Natural Products Chemistry, School of Pharmaceutical Sciences, Wakayama Medical University, 25-1 Shichibancho, Wakayama, 640-8156, Japan. s_tamura@wakayama-med.ac.jp.ORCID http://orcid.org/0000-0002-2762-1793

Funding

JSPS KAKENHI 19K05718The foundation for Japanese Chemical Research 482(R)
6 · The paper itself

Abstract

The relative configuration of the epoxide functionality in pinofuranoxin A (1), α-alkylidene-β-hydroxy-γ-methyl-γ-butyrolactone with trans-epoxy side chain isolated by Evidente et al. in 2021, was revised by DFT-based spectral reinvestigations and stereo-controlled synthesis. The present investigation demonstrates the difficulty of the configurational elucidation of the stereogenic centers on the conformationally flexible acyclic side-chains. Sharpless's enantioselective epoxidations and dihydroxylations were quite effective in the reinvestigations of the configurations. As our syntheses made all diastereomers available, these would be quite effective in the next structure-biological activity relationship studies.

Indexed as

4-ButyrolactoneMolecular ConformationMolecular StructureStereoisomerismStructure-Activity Relationship4-ButyrolactoneAsymmetric synthesisPinofuranoxin ASpectroscopic comparison among stereoisomersStructure correction

Identifiers

PMID38587582

What OpenQuestion holds

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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.