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Record W4410507659 · doi:10.1039/d5sc02953h

Bio-inspired total synthesis of daphnepapytone A

2025· article· en· W4410507659 on OpenAlexfundno aff
Nicolas Casaretto, Gilles Frison, Bastien Nay

Bibliographic record

VenueChemical Science · 2025
Typearticle
Languageen
FieldChemistry
TopicChemical synthesis and alkaloids
Canadian institutionsnot available
FundersCentre National de la Recherche ScientifiqueAgence Nationale de la RechercheUniversité de Sherbrooke
KeywordsTotal synthesisSesquiterpeneSkeleton (computer programming)ChemistryStereochemistryComputer scienceProgramming language

Abstract

fetched live from OpenAlex

to give the guaiane skeleton. Oleodaphnone (3) was identified as a key intermediate of this strategy and was engaged in a biomimetic [2 + 2]-photocycloaddition, leading to the bridged cyclobutane of the title compound. Finally, a late-stage C-H oxidation chemoselectively released a triketone intermediate (15), which was reduced in a remarkably chemo- and stereoselective manner to furnish target compound 1. During this work, complex rearrangements of the bridged skeleton were observed. Beside the total synthesis of daphnepapytone A, this paper also describes the total synthesis of three guaiane natural products (oleodaphnone, diarthroncha C, daphnenicillata W), one of them being structurally revised.

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)0.000
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 score0.102
Threshold uncertainty score0.749

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.001
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.001
Science and technology studies0.0000.001
Scholarly communication0.0000.000
Open science0.0010.000
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 head0.007
GPT teacher head0.239
Teacher spread0.232 · 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
Published2025
Admission routes1
Has abstractyes

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