Heterocycles via C–H functionalization strategies; synthesis of pyrroloindoles and tanshinone IIA
Bibliographic record
Abstract
This thesis is divided into two projects. Chapter one discusses the development of tandem C–H functionalization and Michael-type annulation using α-diazocarbonyl compounds for the synthesis of fused indole ring systems. Highlights include the use of cheap copper catalysts, high stereoselectivity, and a robust substrate scope showcasing the amenability of the transformation to various indole and diazo substrates. Details of an interesting base-catalyzed olefin isomerization will also be discussed. Chapter two details a newly developed total synthesis of tanshinone IIA, an abietane diterpenoid from the tanshinone family of natural products. This route is highlighted by access to complex coupling partners through multigram scale reactions starting from simple commercially available starting materials. Key transformations include an iridium-catalyzed borylation, a directed metalation/iodination, and a Brook-type rearrangement to furnish a synthetically challenging ortho-quinone ring. Chapter three presents a summary of this thesis work and potential avenues for future research.
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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) | 0.000 | 0.000 |
| Bibliometrics | 0.001 | 0.002 |
| Science and technology studies | 0.001 | 0.001 |
| Scholarly communication | 0.000 | 0.001 |
| Open science | 0.001 | 0.001 |
| Research integrity | 0.000 | 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".