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Record W4221034050 · doi:10.1126/science.abn8343

Concise syntheses of GB22, GB13, and himgaline by cross-coupling and complete reduction

2022· article· en· W4221034050 on OpenAlex
Eleanor M. Landwehr, Meghan A. Baker, Takuya Oguma, Hannah E. Burdge, Takahiro Kawajiri, Ryan A. Shenvi

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.

fundA Canadian funder is recorded on the work.
no affNo Canadian affiliation: this work is invisible to an affiliation-only frame.
No Canadian affiliation. An affiliation-only frame, the usual design, would never have seen this work. It is one of the works that make the case for inverting the frame.

Bibliographic record

VenueScience · 2022
Typearticle
Languageen
FieldBiochemistry, Genetics and Molecular Biology
TopicTraditional and Medicinal Uses of Annonaceae
Canadian institutionsnot available
FundersDivision of ChemistryNational Institute of General Medical SciencesShionogiConcordia University of EdmontonJapan Society for the Promotion of ScienceIndustrial Technology Research InstituteBristol-Myers SquibbNational Institutes of HealthNational Science Foundation
KeywordsReduction (mathematics)Bark (sound)ChemistryCoupling (piping)StereochemistryBiologyMaterials scienceMathematics

Abstract

fetched live from OpenAlex

Neuroactive metabolites from the bark of Galbulimima belgraveana occur in variable distributions among trees and are not easily accessible through chemical synthesis because of elaborate bond networks and dense stereochemistry. Previous syntheses of complex congeners such as himgaline have relied on iterative, stepwise installation of multiple methine stereocenters. We decreased the synthetic burden of himgaline chemical space to nearly one-third of the prior best (7 to 9 versus 19 to 31 steps) by cross-coupling high fraction aromatic building blocks (high F sp 2) followed by complete, stereoselective reduction to high fraction sp 3 products (high F sp 3). This short entry into Galbulimima alkaloid space should facilitate extensive chemical exploration and biological interrogation.

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)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesnone
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 score0.179
Threshold uncertainty score0.276

Codex and Gemma teacher scores by category

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

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 head0.017
GPT teacher head0.272
Teacher spread0.256 · 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