Stereocontrolled Carbocyclic Construction: The Mulzer Synthesis of (-)-Penifulvin A
Bibliographic record
Abstract
Tanmaya Pathak of the Indian Institute of Technology, Kharagpur devised (J. Org. Chem. 2009, 74, 2710) a preparation of enantiomerically-pure oxygenated cyclopropanes such as 3 from carbohydrate precursors. Andrei K. Yudin of the University of Toronto established (Organic Lett. 2009, 11, 1281) a route to aminated cyclobutanes such as 5 based on sigmatropic rearrangement of the β-lactam 4. Tanmaya Pathak of the Indian Institute of Technology, Kharagpur devised ( J. Org. Chem. 2009 , 74 , 2710) a preparation of enantiomerically-pure oxygenated cyclopropanes such as 3 from carbohydrate precursors. Andrei K. Yudin of the University of Toronto established (Organic Lett . 2009 , 11 , 1281) a route to aminated cyclobutanes such as 5 based on sigmatropic rearrangement of the β -lactam 4 . Stephen C. Bergmeier of Ohio University reported (Tetrahedron 2009, 65, 741) a study of the balance between five- and six-membered ring formation in the cyclization of aziridines such as 6. Professor Bergmeier also described (Tetrahedron Lett. 2009, 50, 1261) the bridging additions of enones to cyclic allyl silanes such as 8. This is particularly interesting, as 8 is easily prepared by Birch reduction of the corresponding phenyl silane. Ullrich Jahn of the Academy of Sciences of the Czech Republic observed (Chem. Eur. J. 2009, 15, 58) that the free-radical cyclization of 11 proceeded to give mainly the diastereomer 12 (~ 1:1 at the secondary allylic position). Daesung Lee of the University of Illinois at Chicago reasoned (J. Am. Chem. Soc. 2009, 131, 8413) that the stereochemical relationship between the O and the adjacent C-H of 13 was such that the C-H would be deactivated. The cyclization of the alkylidene carbene derived from 13 indeed proceeded to give 14, setting the stage for the synthesis of platensimycin. Marco A. Cufolini of the University of British Columbia found (Organic Lett . 2009, 11, 1539) an easy protocol for the generation of a nitrile oxide and subsequent dipolar cycloaddition, by oxidation of the oxime.
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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) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.001 | 0.001 |
| Insufficient payload (model declined to judge) | 0.001 | 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".