Carbon–Carbon Bond Construction: The Baran Synthesis of (+)-Chromazonarol
Bibliographic record
Abstract
Daniel J. Weix of the University of Rochester effected (Org. Lett. 2012, 14, 1476) the in situ reductive coupling of an alkyl halide 2 with an acid chloride 1 to deliver the ketone 3. André B. Charette of the Université de Montréal (not illustrated) developed (Nature Chem. 2012, 4, 228) an alternative route to ketones by the coupling of an organometallic with an in situ-activated secondary amide. Mahbub Alam and Christopher Wise of the Merck, Sharpe and Dohme UK chemical process group optimized (Org. Process Res. Dev. 2012, 16, 453) the opening of an epoxide 4 with a Grignard reagent 5. Ling Song of the Fujian Institute of Research on the Structure of Matter optimized (J. Org. Chem. 2012, 77, 4645) conditions for the 1,2-addition of a Grignard reagent (not illustrated) to a readily enolizable ketone. Wei-Wei Liao of Jilin University conceived (Org. Lett. 2012, 14, 2354) of an elegant assembly of highly functionalized quaternary centers, as illustrated by the conversion of 7 to 8. Antonio Rosales of the University of Granada and Ignacio Rodríguez-García of the University of Almería prepared (J. Org. Chem. 2012, 77, 4171) free radicals by reduction of an ozonide 9 in the presence of catalytic titanocene dichloride. In the absence of the acceptor 10, the dimer of the radical was obtained, presenting a simple alternative to the classic Kolbe coupling. Marc L. Snapper of Boston College found (Eur. J. Org. Chem. 2012, 2308) that the difficult ketone 12 could be methylenated following a modified Peterson protocol. Yoshito Kishi of Harvard University optimized (Org. Lett. 2012, 14, 86) the coupling of 15 with 16 to give 17. Masaharu Nakamura of Kyoto University devised (J. Org. Chem. 2012, 77, 1168) an iron catalyst for the coupling of 18 with 19. The specific preparation of trisubsituted alkenes is an ongoing challenge. Quanri Wang of Fudan University and Andreas Goeke of Givaudan Shanghai fragmented (Angew. Chem. Int. Ed. 2012, 51, 5647) the ketone 21 by exposure to 22 to give the macrolide 23 with high stereocontrol.
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How this classification was reachedexpand
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 | 0.001 |
| 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) | 0.000 | 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 itClassification
machine, unvalidatedMachine predicted; a candidate call from one teacher head, not a consensus.
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".