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Record W2949320033 · doi:10.1055/s-0033-1339926

Short, Enantioselective Total Syntheses of Fugomycin and Desoxyfugomycin via Sonogashira Alkynylation of α-Bromobutenolides

2013· article· en· W2949320033 on OpenAlexafffund
John Boukouvalas, Nicolas Bruneau‐Latour

Bibliographic record

VenueSynlett · 2013
Typearticle
Languageen
FieldChemistry
TopicSynthetic Organic Chemistry Methods
Canadian institutionsUniversité Laval
FundersNatural Sciences and Engineering Research Council of CanadaAgricultural Research ServiceFonds Québécois de la Recherche sur la Nature et les TechnologiesCentre in Green Chemistry and Catalysis
KeywordsChemistrySonogashira couplingEnantioselective synthesisRacemizationAlkynylationAntifungalCombinatorial chemistryTotal synthesisStereochemistryOrganic chemistryPalladiumCatalysis

Abstract

fetched live from OpenAlex

The potent antifungal antibiotics (+)-fugomycin and (+)-desoxyfugomycin were synthesized in 3–4 steps with high overall efficiency (51–53%) and optical purity (ee > 97%). The syntheses illustrate a highly effective protocol for accomplishing racemization-free Sonogashira coupling of chiral α-bromobutenolides, and the usefulness of the Movassaghi–Jacobsen method for preparing the latter from epoxides.

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 categoriesInsufficient payload (model declined to judge)
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 score0.045
Threshold uncertainty score0.999

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.001
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0020.000

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 head0.236
Teacher spread0.223 · 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.

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

Citations4
Published2013
Admission routes2
Has abstractyes

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