Organoboron-Based Allylation\nApproach to the Total\nSynthesis of the Medium-Ring Dilactone (+)-Antimycin A<sub>1b</sub>
Bibliographic record
Abstract
The stereoselective synthesis of\n(+)-antimycin A<sub>1b</sub> has\nbeen accomplished in 12 linear steps and 18% overall yield from (−)-ethyl\nlactate. A robust, scalable, and highly diastereoselective montmorillonite\nK10-promoted allylation reaction between an α-silyloxy aldehyde\nand a substituted potassium allyltrifluoroborate salt provides a general\napproach to the core stereochemical triad of the antimycin A family.\nThe requisite (Z)-substituted potassium allyltrifluoroborate salt\nwas synthesized using a <i>syn</i>-selective hydroboration/protodeboration\nof an alkynylboronate ester, followed by a Matteson homologation reaction.\nThe total synthesis leverages an MNBA (Shiina’s reagent)-mediated\nmacrolactonization to generate the 9-membered dilactone ring and a\nlate-stage PyBOP-mediated amide coupling employing an unprotected\n3-formamidosalicylic acid fragment, thereby shortening the longest\nlinear sequence and, perhaps most notably, generating the antimycin\nA C7–C8–C9 stereotriad in a single step using a single\nchiral pool-derived stereocenter.
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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) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.001 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.012 | 0.001 |
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; both teacher heads agree on what is shown here.
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".