{"id":"W2889911904","doi":"10.1039/c8qo00849c","title":"Enantioselective isoquinuclidine synthesis <i>via</i> sequential Diels–Alder/visible-light photoredox C–C bond cleavage: a formal synthesis of the indole alkaloid catharanthine","year":2018,"lang":"en","type":"article","venue":"Organic Chemistry Frontiers","topic":"Alkaloids: synthesis and pharmacology","field":"Pharmacology, Toxicology and Pharmaceutics","cited_by":20,"is_retracted":false,"has_abstract":true,"ca_institutions":"University of Toronto; Toronto Public Health","funders":"Natural Sciences and Engineering Research Council of Canada","keywords":"Chemistry; Enantioselective synthesis; Alkaloid; Indole test; Acrolein; Cleavage (geology); Bond cleavage; Oxidative cleavage; Photoredox catalysis; Diels–Alder reaction; Stereochemistry; Organic chemistry; Combinatorial chemistry; Catalysis; Photocatalysis","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":"metacan-v3-hybrid-931329e0061c","candidate_categories":[],"consensus_categories":[],"category_scores_codex":[0.0002655043,0.0005380869,0.0002757911,0.0002101797,0.0001967105,0.0002570964,0.0005032593,0.0004418435,0.001796332],"category_scores_gemma":[0.0002097757,0.0002086092,0.0003684431,0.0001672706,0.0002645461,0.0003235688,0.0003233773,0.0006154454,0.001060391],"about_ca_system_candidate":false,"about_ca_system_consensus":false,"about_ca_system_score_codex":0.0003845541,"about_ca_system_score_gemma":0.0002688566,"about_ca_topic_candidate":false,"about_ca_topic_consensus":false,"about_ca_topic_score_codex":0.0006038112,"about_ca_topic_score_gemma":0.0009920544,"domain_scores_codex":[0.9997548,0.00003397746,0.00002319193,0.00006410718,0.00005899245,0.00006485543],"domain_scores_gemma":[0.99991,0.00001070613,0.00002602125,0.00002079162,0.00001754454,0.00001503623],"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":[0.00003904348,0.0000259125,0.00006259143,0.0001147696,0.00001000498,0.0002434277,0.00006752725,0.0002070431,0.991927,0.001388687,0.0002181537,0.005695847],"study_design_scores_gemma":[0.00001610015,0.0001834903,0.0003688679,0.000004795205,0.000007466323,0.0004184797,0.00002007066,0.0004294977,0.9929661,0.0001879198,0.005381739,0.0000155634],"study_design_candidate":"bench_or_experimental","study_design_consensus":"bench_or_experimental","genre_codex":"empirical","genre_gemma":"empirical","genre_scores_codex":[0.8434639,0.005317014,0.1057633,0.0007011812,0.0004757315,0.0004281042,0.001451027,0.001188359,0.0412114],"genre_scores_gemma":[0.9725189,0.001831119,0.0204793,0.00009679986,0.00002850517,0.00006456525,0.000438121,0.00008787281,0.004454809],"genre_candidate":"empirical","genre_consensus":"empirical","teacher_disagreement_score":0.001796332,"threshold_uncertainty_score":0.00600934,"prediction_status":"machine_predicted_unvalidated"},"machine_scores":{"provisional":true,"baseline":true,"maturity_gate_passed":false,"score_opus":0.02278022350149035,"score_gpt":0.3082098079969339,"score_spread":0.2854295844954436,"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."}}