Stereoselective C-O Ring Construction: The Jamison Synthesis of (-)-Gloeosporone
Bibliographic record
Abstract
Arene diazonium salts are effective precursors for the Heck reaction. Sandro Cacchi of the Università degli Studi “La Sapienza,” Roma, observed (Synlett 2009, 1277) that the diazonium salt generated in situ from 1 coupled with 2 to deliver the butenolide 3. Daniel J. Canney of Temple University established (Tetrahedron Lett. 2009, 50, 5914) conditions for the homologation of an alkenyl ester such as 4 to the homologated lactone 5. Tsutomu Katsuki of Kyushu University established (J. Am. Chem. Soc. 2009, 131, 14218) that Ir-mediated C-H insertion converted 6 into 8 with high diastereo- and enantiocontrol. Thomas J. J. Müller of the Heinrich-Heine-Universität, Düsseldorf, optimized ( Adv. Synth. Cat. 2009, 351, 2921) the Rh-mediated enantioselective cycloisomerization of 9 to 10. Santosh J. Gharpure of the Indian Institute of Technology, Madras, showed (Organic Lett. 2009, 11, 5466) that the intramolecular cyclopropanation of 11 proceeded with high diasterocontrol. Reduction of the intermediate cyclopropane then delivered the cyclic ether 12. Brian L. Pagenkopf of the University of Western Ontario optimized (Organic Lett. 2009, 11, 5614) the diastereoselective Co-catalyzed oxidative cyclization of 13 to 14. Mark C. Bagley and Andrew E. Graham of Cardiff University found (Tetrahedron Lett. 2009, 50, 6823) that microwave heating promoted the selective BaMnO4 oxidation of 1,3-, 1,4-, and 1,5-diols such as 15 to the corresponding lactones. David W. Lupton of Monash University developed (J. Am. Chem. Soc. 2009, 131, 14176) the remarkable cyclization of 17 to 19, catalyzed by the carbene precursor 18. Hirokazu Urabe of the Tokyo Institute of Technology showed (J. Am. Chem. Soc. 2009, 131, 3166) that the unusual Rh-catalyzed cyclization of an alkynyl sulfone 20 proceeded with substantial diastereocontrol, delivering the cyclic ether 21 as the major product. Jeffrey S. Johnson of the University of North Carolina established (J. Am. Chem. Soc. 2009, 131, 14202) that Sc(OTf)3 was a particularly efficient catalyst for the opening of 22 with 23 and then reclosure, leading to 24. Steven D. R. Christie and Gareth J. Pritchard of Loughborough University (Chem. Commun. 2009, 7339) and Michael A. Kerr of the University of Western Ontario (J. Org. Chem. 2009, 74, 8414) investigated related condensations.
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How this classification was reachedexpand
Full frame machine prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.
Distilled classifier scores by category (both heads)
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.000 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.001 |
| Research integrity | 0.000 | 0.001 |
| Insufficient payload (model declined to judge) | 0.003 | 0.002 |
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 source (direct Gemma or distilled Codex), 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".