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Record W1606711676 · doi:10.1002/ejoc.201402331

5‐Aminopenta‐2,4‐dienals: Synthesis, Activation towards Nucleophiles, Molecular Modeling and Biosynthetic Implications in Relation to the Manzamine Alkaloids

2014· article· en· W1606711676 on OpenAlexaff
Lok‐Hang Yan, Adam Skiredj, Yves L. Dory, Bernard Delpech, Erwan Poupon

Bibliographic record

VenueEuropean Journal of Organic Chemistry · 2014
Typearticle
Languageen
FieldChemistry
TopicChemical synthesis and alkaloids
Canadian institutionsUniversité de Sherbrooke
Fundersnot available
KeywordsNucleophileElectrophileChemistryIminiumPyridiniumReactivity (psychology)HOMO/LUMOStereochemistryOrganic chemistryMoleculeCatalysis

Abstract

fetched live from OpenAlex

Abstract Substituted 5‐aminopentadienals and glutaconaldehydes are key elements postulated in the biosynthesis of the diverse class of manzamine‐type alkaloids. The activation of 5‐aminopentadienals into electrophilic iminium salts and their subsequent reactivity towards various nucleophiles has permitted the synthesis of a series of unsaturated compounds sometimes accompanied by cascades of rearrangements. Molecular modeling of these systems carried out using DFT calculations of HOMO/LUMO was in agreement with the experimental results indicating that strong electrophilic agents, such as POCl 3 are required to turn 5‐aminopentadienals into electrophiles. New examples of glutaconaldehyde reactivity, especially towards pyridinium salts, are presented and biosynthetic considerations are kept in mind throughout this study.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.001
metaresearch head score (Gemma)0.001
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.023
Threshold uncertainty score0.703

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.001
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0010.000

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.012
GPT teacher head0.212
Teacher spread0.200 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one teacher head, not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designBench or experimental
Domainnot available
GenreEmpirical

How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".

Quick stats

Citations6
Published2014
Admission routes1
Has abstractyes

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