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Record W2130208417 · doi:10.1002/ejoc.200600674

Aporphine Alkaloid Synthesis and Diversification via Direct Arylation

2006· article· en· W2130208417 on OpenAlex
Marc Lafrance, Nicole Blaquière, Keith Fagnou

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.
fundA Canadian funder is recorded on the work.

Bibliographic record

VenueEuropean Journal of Organic Chemistry · 2006
Typearticle
Languageen
FieldBiochemistry, Genetics and Molecular Biology
TopicTraditional and Medicinal Uses of Annonaceae
Canadian institutionsUniversity of Ottawa
FundersNatural Sciences and Engineering Research Council of CanadaGovernment of OntarioUniversity of Ottawa
KeywordsChemistryEnantioselective synthesisAporphinePyrazineCatalysisPyridineOrganic chemistryPalladiumYield (engineering)AlkaloidCombinatorial chemistryStereochemistry

Abstract

fetched live from OpenAlex

Abstract Palladium‐catalyzed direct arylation of aryl chlorides, bromides and iodides has been applied to the preparation of new aporphine analogues including C2‐substituted aporphines by reaction with benzodioxole, pyridine N ‐oxide and pyrazine N ‐oxide. Successful application of direct arylation in these diversification reactions highlights its utility not only in convergent, but also in divergent synthesis. We also describe enantioselective syntheses of ( R )‐nornuciferine and ( R )‐nuciferine employing a catalytic asymmetric transfer hydrogenation in high yield and excellent enantiomeric excess. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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.

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)0.000
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 score0.082
Threshold uncertainty score0.328

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
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)0.0000.000

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 head0.005
GPT teacher head0.175
Teacher spread0.170 · 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