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Record W2903767518 · doi:10.1021/acsomega.8b02994

Benefits of Unconventional Methods in the Total Synthesis of Natural Products

2018· review· en· W2903767518 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.
fundA Canadian funder is recorded on the work.

Bibliographic record

VenueACS Omega · 2018
Typereview
Languageen
FieldChemistry
TopicChemical synthesis and alkaloids
Canadian institutionsBrock University
FundersNatural Sciences and Engineering Research Council of CanadaTDC Research FoundationOntario Partnership for Innovation and CommercializationU.S. Environmental Protection AgencyBrock UniversityNational Institutes of HealthUniversity of FloridaCanada Research ChairsCanada Foundation for InnovationVirginia Polytechnic Institute and State UniversityResearch Corporation for Scientific AdvancementThomas F. and Kate Miller Jeffress Memorial TrustTDC Researchllinois Institute of TechnologyAmerican Chemical Society Petroleum Research FundNational Science Foundation
KeywordsEnantioselective synthesisTotal synthesisContext (archaeology)ChemistryOrganic chemistryPyrrolizidineCyclopenteneCombinatorial chemistryBiochemical engineeringCatalysisStereochemistryEngineeringBiology

Abstract

fetched live from OpenAlex

This article provides a survey of four "unconventional" methods employed in the synthesis of natural products in the Hudlicky group. The utility of flash vacuum pyrolysis is highlighted by examples of many natural products attained via vinylcyclopropane-cyclopentene rearrangement and its heterocyclic variants. Preparative organic electrochemistry was used in oxidations and reductions with levels of selectivity unattainable by conventional methods. Yeast reduction of ketoesters was featured in the total synthesis of pyrrolizidine alkaloids. Finally, the use of toluene dioxygenase-mediated dihydroxylations in enantioselective synthesis of natural products concludes this presentation. Recently, synthesized targets in the period 2010-2019 are listed in the accompanying table. The results of research from the Hudlicky group are placed in appropriate context with the work of others, and a detailed guide to the current literature is provided.

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)0.002
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Other design · Consensus signal: none
GenreCandidate signal: Review · Consensus signal: Review
Teacher disagreement score0.974
Threshold uncertainty score0.751

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.002
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)0.0000.000

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 head0.050
GPT teacher head0.345
Teacher spread0.296 · 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