Synthesis and utilization of novel diazo-enones; total synthesis of furan-based target molecules
Bibliographic record
Abstract
This thesis focuses mainly on the synthesis and application of diazo compounds. More specifically, a unique subclass of α-diazocarbonyl compounds, known as diazo-enones. This category features both an α,β-unsaturated carbonyl moiety and a diazo group. These multifunctional compounds can be utilized as Michael acceptors, dienophiles, or carbene precursors, enabling the construction of complex organic compounds. This work focuses on developing a new method for synthesizing acceptor-type diazo-enone and its β-substituted derivatives without using diazomethane. Additionally, exploring their application in the construction of polycyclic heteroaromatic compounds through a novel Hauser-Kraus type annulation. Traditionally, the Hauser-Kraus reaction involves a [4 + 2] cycloaddition between phthalides and α,β-unsaturated carbonyl compounds to build naphthalene derivatives. Here, diazo-enones serve as surrogates for the classical α,β-unsaturated compounds, leading to the efficient synthesis of naphthofuran scaffold via construction of two C–C and one C–O bonds in one step. This structural motif is found in many natural products such as furomollugin. This thesis also covers the total synthesis of the antimicrobial natural product isomicrocionine-3. This synthetic route features a novel 3-substituted furan construction via a monowave-mediated [4 + 2]/retro-[4 + 2] reaction, furnishing the natural product in a 7 step convergent synthesis.
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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 | 0.001 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 0.000 |
| Bibliometrics | 0.001 | 0.001 |
| Science and technology studies | 0.001 | 0.001 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| 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".