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Record W1986114029 · doi:10.1021/jo015643r

Cyclopentannulation of 3-Alkylindoles:  A Synthesis of a Tetracyclic Subunit of the Kopsane Alkaloids

2001· article· en· W1986114029 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 · 2001
Typearticle
Languageen
FieldChemistry
TopicChemical synthesis and alkaloids
Canadian institutionsWestern University
Fundersnot available
KeywordsSubstituentCyclopropaneChemistrySteric effectsAlkylAnnulationStereochemistryMedicinal chemistryOrganic chemistryRing (chemistry)Catalysis

Abstract

fetched live from OpenAlex

Indoles which bear an alkyl substituent in the 3-position undergo a [3 + 2] annulation reaction when treated with 1,1-cyclopropane diesters in the presence of Yb(OTf)(3) resulting in 2,3-cyclopentanoindolines. Typically, the reactions are performed at elevated temperatures or at ultrahigh pressures. In cases where steric crowding is an issue, ultrahigh pressures are required. In reactions involving substituted cyclopropanes, significant regio- and diastereocontrol was observed. When the substituent was aromatic or olefinic, the reactions took place at ambient temperature and pressure. The applicability of this methodology to the preparation of a key tetracyclic subunit of the kopsane alkaloids was demonstrated.

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)0.001
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 score0.006
Threshold uncertainty score0.997

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.001
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0040.000

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 head0.008
GPT teacher head0.209
Teacher spread0.201 · 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