Evidence map›Paper›PMID 40761026›Full record

ArticleAngewandte Chemie (International ed. in English)2025

Exo-Selective Intramolecular (4+3) Cycloadditions to Trans-Fused Perhydroazulenes: An Asymmetric Formal Synthesis of (-)-Pseudolaric Acid B.

Zengsheng Yin, Yuxuan He, Guo Wei, Yuchen Zhou, Antonio Rizzo, Yun He, Elizabeth H Krenske, Pauline Chiu

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. Cited by 3 papers.

0numbers the graph read from it
0cells of the map it votes in
3citing 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

3 citing papers in PubMed.

  1. Article
  2. Article
  3. 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.

Zengsheng YinDepartment of Chemistry, and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P.R. China.
Yuxuan HeDepartment of Chemistry, and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P.R. China.
Guo WeiDepartment of Chemistry, and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P.R. China.
Yuchen ZhouSchool of Chemistry and Molecular Biosciences, The University of Queensland, St Lucia, QLD, 4072, Australia.
Antonio RizzoDepartment of Chemistry, and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P.R. China.ORCID https://orcid.org/0000-0002-3626-9429
Yun HeDepartment of Chemistry, and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P.R. China.
Elizabeth H KrenskeSchool of Chemistry and Molecular Biosciences, The University of Queensland, St Lucia, QLD, 4072, Australia.ORCID https://orcid.org/0000-0003-1911-0501
Pauline ChiuDepartment of Chemistry, and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P.R. China.ORCID https://orcid.org/0000-0001-5081-4756

Funding

General Research Fund from the Research Grants Council of Hong Kong 17309320Laboratory for Synthetic Chemistry and Chemical BiologyNational Computational InfrastructureNational Natural Science Foundation of China 21672179State Key Laboratory of Synthetic Chemistry
6 · The paper itself

Abstract

We present an asymmetric formal total synthesis of pseudolaric acid B (PAB), based on the intramolecular (4+3) cycloaddition of a new class of epoxy enolsilane substrates. This substrate type has the epoxide geminally-substituted on the tether to the furan, which reacts to yield the trans-fused perhydroazulene core of PAB containing the quaternary stereocenter. The reaction is highly diastereoselective, as opposed to cycloadditions of previous substrate types that generate the perhydroazulene framework. The role of the geminal tether in controlling the transition state conformation and the exo-selectivity is revealed by density functional theory calculations. Using this intramolecular cycloaddition as the key reaction, together with several one-pot sequences, a key intermediate in Trost's synthesis of PAB was accomplished, representing the shortest asymmetric synthesis of this anti-tumor natural product thus far.

Indexed as

(4+3) cycloadditionNatural productsOne‐pot reactionsPseudolaric acidsTotal synthesis

Identifiers

PMID40761026
PMCPMC12435416

What OpenQuestion holds

Textmetadata
LicenceCC BY
Read underepoch 390

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.