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Record W6903236019 · doi:10.1021/jo900922q.s001

Pentacyclic Furanosteroids: The Synthesis of Potential Kinase Inhibitors Related to Viridin and Wortmannolone

2016· article· en· W6903236019 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

VenueFigshare · 2016
Typearticle
Languageen
FieldChemistry
TopicOrganic Chemistry Synthesis Methods
Canadian institutionsUniversity of Waterloo
Fundersnot available
KeywordsIntramolecular forceSubstituentNitrileDihydroxylationRing (chemistry)Natural productDouble bond

Abstract

fetched live from OpenAlex

A regiocontrolled intermolecular Diels−Alder reaction of an <i>o</i>-benzoquinone followed by an intramolecular nitrile oxide cyclization is employed to prepare the BCD fragment of viridin. The AE segment is attached to it by means of an intramolecular Diels−Alder reaction of an <i>o</i>-benzoquinone monoketal generated in situ from tricycle <b>15</b> and 5-trimethylsilyl-2<i>E</i>,4<i>E</i>-pentadienol <b>20</b>. The silyl substituent at C-1 of the pentacyclic product directs the dihydroxylation of the C<sub>2</sub>−C<sub>3</sub> double bond to its β-face. Various transformations of the 1α-trimethylsilyl-2β,3β-dihydroxy pentacycle into several others with oxygen substituents in ring A are described. One of these products <b>40</b> possesses the same structure and relative stereochemistry in rings A, B, and E as that of the natural product wortmannolone <b>3</b>.

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)0.004
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 score0.131
Threshold uncertainty score0.870

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.004
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)0.1310.000

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 head0.014
GPT teacher head0.246
Teacher spread0.231 · 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