Intramolecular Tricarbonyl-Ene Reactions and α-Hydroxy-β-Diketone Rearrangements Inspired by the Biosynthesis of Polycyclic Polyprenylated Acylphloroglucinols.

Andreas B Zur Bonsen, Ricardo A Peralta, Thomas Fallon, David M Huang, Jonathan H George

Abstract read

In one paragraph

Article in Angewandte Chemie (International ed. in English), 2022. 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

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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.

Intramolecular Tricarbonyl-Ene Reactions and α-Hydroxy-β-Diketone Rearrangements Inspired by the Biosynthesis of Polycyclic Polyprenylated Acylphloroglucinols.Angewandte Chemie (International ed. in English) · 2022
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

5 authors.

Andreas B Zur BonsenDepartment of Chemistry, The University of Adelaide, Adelaide, SA 5005, Australia.

Ricardo A PeraltaDepartment of Chemistry, The University of Adelaide, Adelaide, SA 5005, Australia.

Thomas FallonDepartment of Chemistry, The University of Adelaide, Adelaide, SA 5005, Australia.

David M HuangDepartment of Chemistry, The University of Adelaide, Adelaide, SA 5005, Australia.

Jonathan H GeorgeDepartment of Chemistry, The University of Adelaide, Adelaide, SA 5005, Australia.ORCID 0000-0002-7330-2160

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Structurally unique natural products pose biosynthetic puzzles whose solution can inspire new chemical reactions. Herein, we propose a unified biosynthetic pathway towards some complex meroterpenoids-the hyperireflexolides, biyoulactones, hybeanones and hypermonones. This hypothesis led to the discovery of uncatalyzed, intramolecular carbonyl-ene reactions that are spontaneous at room temperature. We also developed an anionic cascade reaction featuring an α-hydroxy-β-diketone rearrangement and an intramolecular aldol reaction to access four distinct natural product scaffolds from a common intermediate.

Indexed as

Biological ProductsKetonesCyclizationBiological ProductsKetonesBiomimetic SynthesisCarbonyl-Ene ReactionCascade ReactionsNatural ProductsRearrangement

Identifiers

PMID35680561

DOI10.1002/anie.202203311

PMCPMC9541541

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