Stereocontrolled C-N Ring Construction: The Pyne Synthesis of Hyacinthacine B 3
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.
Bibliographic record
Abstract
Keiji Maruoka of Kyoto University found (Organic Lett. 2010, 12, 1668) that the diazo amide 1 derived from the Oppolzer sultam condensed with the imine 2 to give the aziridine 3 with high stereocontrol. Andrei K. Yudin of the University of Toronto observed (Angew. Chem. Int. Ed. 2010, 49, 1607) that the unprotected aziridine aldehyde 4, which exists as a mixture of dimers, condensed smoothly with the Ohira reagent 5 to give the alkynyl aziridine 6. David M. Hodgson of the University of Oxford successfully (Angew. Chem. Int. Ed. 2010, 49, 2900) deprotonated the azetidine thioamide 7 to give, after allylation, the azetidine 8. Varinder K. Aggarwal of the University of Bristol devised (Chem. Commun. 2010, 267) a Pd catalyst for the cyclocarbonylation of an alkenyl aziridine 9 to give the β-lactam 10. Iain Coldham of the University of Sheffield used (J. Org. Chem. 2010, 75, 4069) the ligand they had developed to effect enantioselective allylation of the pyrrolidine derivative 11. The corrresponding piperidine worked as well. John P. Wolfe of the University of Michigan established (Organic Lett. 2010, 12, 2322) that the Pd-mediated cyclization of 13 to 15 could be effected with high diastereocontrol. Christopher G. Frost of the University of Bath optimized (Angew. Chem. Int. Ed. 2010, 49, 1825) the tandem Ru-mediated conjugate addition/cyclization of 16 to give 18 in high ee. Barry M. Trost of Stanford University extended (J. Am. Chem. Soc. 2010, 132, 8238) their studies of trimethylenemethane cycloaddition to the ketimine 19, leading to the substituted pyrrolidine 21 in high ee. Pher G. Andersson of Uppsala University optimized (J. Am. Chem. Soc. 2010, 132, 8880) an Ir catalyst for the enantioselective hydrogenation of readily prepared tetrahydropyridines such as 22. Min Shi of the Shanghai Institute of Organic Chemistry devised (J. Org. Chem. 2010, 75, 3935) a Pd catalyst for enantioselective conjugate addition to the prochiral pyridone 24. Xiaojun Huang of Roche Palo Alto prepared (Tetrahedron Lett. 2010, 51, 1554) the monoacid 26 by enantioselective methanolysis of the anhydride. Selective formylation of the ester led to the pyridone 27.
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Full frame distilled prediction
Teacher imitationNot 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.
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.000 |
| Meta-epidemiology (narrow) | 0.001 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.001 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.001 | 0.001 |
| Insufficient payload (model declined to judge) | 0.002 | 0.000 |
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.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it