Evidence map›Paper›PMID 40392258›Full record

ArticleAngewandte Chemie (International ed. in English)2025

Enantioselective Total Synthesis of (-)-Psiguadial A.

Liam P O'Grady, Marcel Achtenhagen, Michael F Wisthoff, Robert S Lewis, Katarina Pfeifer, Weifeng Zheng, Maxwell I Martin, Glenn P A Yap, William J Chain

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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

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

9 authors.

Liam P O'GradyDepartment of Chemistry & Biochemistry, University of Delaware, 163 The Green, Newark, Delaware, 19716, USA.
Marcel AchtenhagenDepartment of Chemistry & Biochemistry, University of Delaware, 163 The Green, Newark, Delaware, 19716, USA.
Michael F WisthoffDepartment of Chemistry & Biochemistry, University of Delaware, 163 The Green, Newark, Delaware, 19716, USA.
Robert S LewisDepartment of Chemistry & Biochemistry, University of Delaware, 163 The Green, Newark, Delaware, 19716, USA.
Katarina PfeiferDepartment of Chemistry & Biochemistry, University of Delaware, 163 The Green, Newark, Delaware, 19716, USA.
Weifeng ZhengDepartment of Chemistry & Biochemistry, University of Delaware, 163 The Green, Newark, Delaware, 19716, USA.
Maxwell I MartinDepartment of Chemistry & Biochemistry, University of Delaware, 163 The Green, Newark, Delaware, 19716, USA.
Glenn P A YapDepartment of Chemistry & Biochemistry, University of Delaware, 163 The Green, Newark, Delaware, 19716, USA.
William J ChainDepartment of Chemistry & Biochemistry, University of Delaware, 163 The Green, Newark, Delaware, 19716, USA.ORCID 0000-0003-0312-6250

Funding

This renovation project will create over 1455 sq. ft. of state- of-the-art reseaP20GM104316 · NIGMS · UNIVERSITY OF DELAWARE · PI SCHMITZ, KARL ROBERT · 2014 to 2024
$26.8M
Pilot Research Subproject ProgramP30GM110758 · NIGMS · UNIVERSITY OF DELAWARE · PI PATEL, SANDEEP · 2014 to 2018
$5.8M
Carbonyls to Cancer TherapeuticsR01CA163287 · NCI · UNIVERSITY OF HAWAII AT MANOA · PI CHAIN, WILLIAM JOHN · 2013 to 2016
$1.1M
High Sensitivity NMR Spectrometer with CryoprobeS10OD025185 · OD · UNIVERSITY OF DELAWARE · PI FOX, JOSEPH M · 2019 to 2019
$930k
Q-Exactive Orbitrap LC-MC/MS SystemS10OD016267 · OD · UNIVERSITY OF DELAWARE · PI JOHNSTON, MURRAY V · 2013 to 2013
$573k
High Performance Digital NMR SpectrometerS10RR026962 · NCRR · UNIVERSITY OF DELAWARE · PI FOX, JOSEPH M · 2010 to 2010
$500k
National Science Foundation CHE0421224National Science Foundation CHE0840401National Science Foundation CHE1048367National Science Foundation CHE1229234National Science Foundation CHE1664954NCI NIH HHS R01 CA163287NCRR NIH HHS S10 RR026962NIGMS NIH HHS P20 GM104316NIGMS NIH HHS P30 GM110758NIH HHS P20GM104316NIH HHS P30GM110758NIH HHS R01CA163287NIH HHS S10 OD016267NIH HHS S10OD016267NIH HHS S10 OD025185NIH HHS S10OD025185NIH HHS S10RR026962
6 · The paper itself

Abstract

The first enantioselective total synthesis of the antiproliferative natural product (-)-psiguadial A is reported. This approach features the enantioselective synthesis of a complex tricyclic terpenoid precursor, the union of that precursor with a polyketide component by an enolate-ortho-quinone methide coupling reaction to form a highly congested carbon─carbon bond, and an acid-mediated intramolecular hydration ring-closure leveraging a fully substituted alkene to generate the unique oxepane core structure of the natural product.

Indexed as

Biological ProductsMolecular StructureStereoisomerismBiological ProductsMeroterpenoidsNatural products synthesisortho‐Quinone methidesStereoselective synthesisUmpolung

Identifiers

PMID40392258
PMCPMC12406147

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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.