MétaCan
Menu
Back to cohort
Record W4376256811 · doi:10.1021/acs.joc.3c00360

A Concise, Gram-Scale Total Synthesis of Protectin DX and Related Labeled Versions via a Key Stereoselective Reduction of Enediyne

2023· article· en· W4376256811 on OpenAlex

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.

Bibliographic record

VenueThe Journal of Organic Chemistry · 2023
Typearticle
Languageen
FieldChemistry
TopicCyclization and Aryne Chemistry
Canadian institutionsUniversité Laval
Fundersnot available
KeywordsSonogashira couplingEnediyneStereoselectivityTotal synthesisGramCombinatorial chemistryChemistryKey (lock)StereochemistryWittig reactionReduction (mathematics)Block (permutation group theory)Computer scienceOrganic chemistryMathematicsCombinatoricsBacteriaBiology

Abstract

fetched live from OpenAlex

We report a gram-scale total synthesis of protectin DX (PDX) following a convergent synthetic route (24 steps) from l -malic acid. This novel synthetic strategy is based on the assembly of three main building blocks using a Sonogashira coupling reaction (blocks A and B) and Wittig olefination (block C) to provide the 22-carbon backbone of PDX. A key stereoselective reduction of enediyne leads to a central E, Z, E -trienic system of PDX and also gives access to its labeled versions (D and T).

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)0.001
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 score0.003
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
Bibliometrics0.0000.001
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 head0.006
GPT teacher head0.205
Teacher spread0.199 · 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