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Record W1963708583 · doi:10.1002/anie.201401117

Cover Picture: Short Chemoenzymatic Total Synthesis of <i>ent</i>‐Hydromorphone: An Oxidative Dearomatization/Intramolecular [4+2] Cycloaddition/Amination Sequence (Angew. Chem. Int. Ed. 17/2014)

2014· paratext· en· W1963708583 on OpenAlexaff
Vimal Varghese, Tomáš Hudlický

Bibliographic record

VenueAngewandte Chemie International Edition · 2014
Typeparatext
Languageen
FieldChemistry
TopicChemical synthesis and alkaloids
Canadian institutionsBrock University
Fundersnot available
KeywordsHydromorphoneIntramolecular forceChemistryCycloadditionAminationStereochemistryTotal synthesisDihydroxylationEnantioselective synthesisOrganic chemistryOpioidCatalysis

Abstract

fetched live from OpenAlex

A 12-step chemoenzymatic total synthesisof ent-hydromorphone from β-bromoethylbenzene is described by T. Hudlicky and V. Varghese in their Communication on page 4355 ff. The key steps consist of enzymatic dihydroxylation, Mitsunobu coupling, and oxidative dearomatization followed by intramolecular [4+2] cycloaddition. This approach holds potential for further optimization of morphine alkaloid syntheses. We acknowledge the legendary efforts of the chemists pictured, who dedicated their careers to the chemistry of morphine. Cover design: Dennis Ceci, Tomas Hudlicky, Jordan Froese (Brock University).

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 categoriesMeta-epidemiology (narrow), Insufficient payload (model declined to judge)
Consensus categoriesInsufficient payload (model declined to judge)
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: none
Teacher disagreement score0.604
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.001
Meta-epidemiology (narrow)0.0010.001
Meta-epidemiology (broad)0.0010.001
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.001
Open science0.0010.000
Research integrity0.0010.001
Insufficient payload (model declined to judge)0.0530.001

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 head0.009
GPT teacher head0.247
Teacher spread0.238 · 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; both teacher heads agree on what is shown here.

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

Citations0
Published2014
Admission routes1
Has abstractyes

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