An Expedient Synthesis of the Antimitotic Natural Products Sarcodictyin and Eleutherobin, and Carbohydrate Analogues
Bibliographic record
Abstract
The eleutherobins and sarcodictyins are diterpenoids that belong to an elite family of microtubule-stabilizing natural products that includes the frontline cancer therapy Taxol. To date, members of this family of natural products have been overlooked as clinical candidates in large part, owing to a lack of material available from natural sources (rare marine invertebrates) or through chemical synthesis. Here, we report a concise synthesis of several members of the eleutherobin and sarcodictyin natural products using an approach that parallels Nature's strategy, with the assembly of a eunicellin intermediate followed by regio- and diastereoselective oxidations. Additionally, we report a collection of eleutherobin carbohydrate analogues that shed light on the relationship between carbohydrate structure and anticancer activity. These efforts should support and inspire the discovery of next-generation microtubule-stabilizing drugs.
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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 | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.001 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 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".