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Record W4289842915 · doi:10.26434/chemrxiv-2022-933w5

Total Synthesis of Ginkgolide C and Formal Synthesis Ginkgolides A and B

2022· preprint· en· W4289842915 on OpenAlexafffund
Louis Barriault, Martin Hébert, Gabriel Bellavance

Bibliographic record

VenueChemRxiv · 2022
Typepreprint
Languageen
FieldMedicine
TopicGinkgo biloba and Cashew Applications
Canadian institutionsUniversity of Ottawa
FundersNatural Sciences and Engineering Research Council of CanadaUniversity of North Carolina at Chapel HillGovernment of Ontario
KeywordsGinkgolidesStereocenterChemistryStereochemistryTotal synthesisGinkgo bilobaOrganic chemistryBiologyEnantioselective synthesisBotanyCatalysis

Abstract

fetched live from OpenAlex

Ginkgolides are diterpenes isolated from ginkgo biloba that exhibit strong PAF antagonistic activity as well as other interesting neuroprotective properties. These natural products possess a compact, highly oxygenated hexacyclic structure with two adjacent quaternary carbon centers, an unusual tert-butyl group, and up to twelve contiguous stereogenic carbon centers. The molecular architecture of ginkgolides, coupled with their remarkable biological profile, continues to be a source of fascination but also presents a formidable challenge for chemical synthesis. Herein, we reported the first total synthesis of ginkgolide C and the formal syntheses of ginkgolides A and B. The key to achieving these syntheses is a careful orchestration of carbon-carbon bond formation, guided by the compact nature of the ginkgolide structure.

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)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow)
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Observational · Consensus signal: none
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.408
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
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 science0.0000.001
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 head0.016
GPT teacher head0.260
Teacher spread0.243 · 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 designObservational
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

Citations0
Published2022
Admission routes2
Has abstractyes

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