Evidence map›Paper›PMID 34305185›Full record

ArticleTetrahedron2021

Synthetic strategy toward ineleganolide: A cautionary tale.

Alexander Q Cusumano, K N Houk, Brian M Stoltz

Abstract read
In one paragraph

Article in Tetrahedron, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.

0numbers the graph read from it
0cells of the map it votes in
5citing 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

5 citing papers in PubMed.

  1. Asymmetric Total Synthesis of (+)-Ineleganolide.Angewandte Chemie (International ed. in English) · 2026
    Article
  2. Short, Enantioselective Total Synthesis of (+)-Ineleganolide.Journal of the American Chemical Society · 2025
    Article
  3. Article
  4. A Convergent Total Synthesis of (+)-Ineleganolide.Journal of the American Chemical Society · 2023
    Article
  5. Total Syntheses of (+)-Ineleganolide and (-)-Sinulochmodin C.Journal of the American Chemical Society · 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

3 authors.

Alexander Q CusumanoDivision of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
K N HoukDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, USA.
Brian M StoltzDivision of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.

Funding

The Synthesis of Bioactive Polycyclic Natural ProductsR01GM080269 · NIGMS · CALIFORNIA INSTITUTE OF TECHNOLOGY · PI STOLTZ, BRIAN M · 2007 to 2022
$5.0M
The Synthesis of Bioactive Natural Products as a Driving Force for Discovery in Organic ChemistryR35GM145239 · NIGMS · CALIFORNIA INSTITUTE OF TECHNOLOGY · PI BRIAN M STOLTZ · 2022 to 2026
$3.1M
NIGMS NIH HHS R01 GM080269NIGMS NIH HHS R35 GM145239
6 · The paper itself

Abstract

We present a case study to demonstrate how complex molecule synthesis can benefit from quantum mechanics (QM) calculations. Theory is applied in two contexts: testing the chemical intuition used in retrosynthetic planning, along with expediting the resolution of unexpected challenges encountered during the course of the synthesis. From a computational lens, we examine retrospectively the strategies employed and the decisions made during our synthetic efforts toward the diterpenoid natural product ineleganolide. Seemingly logical and robust hypotheses are found to be ill-fated after theoretical investigation. Prior knowledge of these issues may have potentially saved valuable time and resources during our synthetic efforts. This cautionary tale suggests that synthetic campaigns can benefit from computational evaluation of synthetic plans.

Indexed as

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Identifiers

PMID34305185
PMCPMC8294177

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.