{"id":"W1975712457","doi":"10.1021/ed100050z","title":"Natural Product Total Synthesis in the Organic Laboratory: Total Synthesis of Caffeic Acid Phenethyl Ester (CAPE), A Potent 5-Lipoxygenase Inhibitor from Honeybee Hives","year":2011,"lang":"en","type":"article","venue":"Journal of Chemical Education","topic":"Various Chemistry Research Topics","field":"Chemistry","cited_by":32,"is_retracted":false,"has_abstract":true,"ca_institutions":"Université de Moncton","funders":"New Brunswick Innovation Foundation","keywords":"Caffeic acid phenethyl ester; Natural product; Chemistry; Total synthesis; Organic synthesis; Recrystallization (geology); Caffeic acid; Mass spectrometry; Lipoxygenase; Arachidonate 5-lipoxygenase; Nuclear magnetic resonance spectroscopy; Organic chemistry; Chromatography; Enzyme; Catalysis; Antioxidant; Biology","routes":{"ca_aff":true,"ca_fund":true,"ca_venue":false,"about_ca":false,"invisible_to_affiliation_only":false},"retraction":null,"screen":null,"direct_labels":[],"prediction":{"model_version":"codex-gemma-dda1882f352a","candidate_categories":[],"consensus_categories":[],"category_scores_codex":[0.0003841858,0.0002593648,0.000436237,0.00009381302,0.0000397445,0.00005207475,0.0006076108,0.0001844287,0.0007023862],"category_scores_gemma":[0.003161496,0.0001923453,0.000193125,0.0003038946,0.0001472881,0.0002760061,0.00008664569,0.0008084576,0.00000948156],"about_ca_system_candidate":false,"about_ca_system_consensus":false,"about_ca_system_score_codex":0.0002949071,"about_ca_system_score_gemma":0.001002426,"about_ca_topic_candidate":false,"about_ca_topic_consensus":false,"about_ca_topic_score_codex":0.00006993453,"about_ca_topic_score_gemma":0.000003955325,"domain_scores_codex":[0.9978085,0.0001078432,0.0007534637,0.0003021155,0.0006985532,0.0003295654],"domain_scores_gemma":[0.9979171,0.0003809273,0.0005915564,0.0005130795,0.0004170939,0.0001802787],"domain_codex":null,"domain_gemma":null,"domain_candidate":null,"domain_consensus":null,"study_design_codex":"bench_or_experimental","study_design_gemma":"bench_or_experimental","study_design_scores_codex":[0.0002146287,0.0009576146,0.001199302,0.0001729989,0.0001057041,0.00001565002,0.002088718,4.692397e-7,0.9872825,0.000003084226,0.0009340387,0.007025354],"study_design_scores_gemma":[0.0002857599,0.00001975808,0.002249328,0.0003074236,0.0001090962,0.000121833,0.001578842,0.00001525823,0.9948773,0.000153063,0.00008428124,0.0001980558],"study_design_candidate":"bench_or_experimental","study_design_consensus":"bench_or_experimental","genre_codex":"empirical","genre_gemma":"empirical","genre_scores_codex":[0.996798,0.001190297,0.000001870785,0.001136593,0.0002500755,0.00009644655,0.00003865772,0.00001184407,0.000476198],"genre_scores_gemma":[0.9974362,0.0000374431,0.001088678,0.00004549163,0.001241942,0.00003315701,0.00001191337,0.00003412905,0.00007100465],"genre_candidate":"empirical","genre_consensus":"empirical","teacher_disagreement_score":0.007594864,"threshold_uncertainty_score":0.7843614,"prediction_status":"machine_predicted_unvalidated"},"machine_scores":{"provisional":true,"baseline":true,"maturity_gate_passed":false,"score_opus":0.01163759633713775,"score_gpt":0.2369722191529802,"score_spread":0.2253346228158425,"validation_status":"score_only:v0-immature-baseline","note":"Baseline scores from an immature model (maturity gate not passed). Scores rank; they never assert a category."}}