{"id":"W2316570170","doi":"10.1021/acs.joc.5b00621","title":"Stereoselective Syntheses of (+)-2-<i>epi</i>-Deoxoprosopinine, (−)-Deoxoprosophylline, (+)-<i>cis</i>-195A, and 2,5-Di-<i>epi</i>-<i>cis</i>-195A from a Common Chiral Nonracemic Building Block","year":2015,"lang":"en","type":"article","venue":"The Journal of Organic Chemistry","topic":"Alkaloids: synthesis and pharmacology","field":"Pharmacology, Toxicology and Pharmaceutics","cited_by":16,"is_retracted":false,"has_abstract":true,"ca_institutions":"University of Regina","funders":"Natural Sciences and Engineering Research Council of Canada; Compute Canada; University of Regina","keywords":"Chemistry; Bicyclic molecule; Stereoselectivity; Stereochemistry; Lactam; Allylic rearrangement; Radical cyclization; Substituent; Hydroxymethyl; Catalysis; Organic chemistry","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":["metaepi_narrow","research_integrity","insufficient_payload"],"consensus_categories":[],"category_scores_codex":[0.002707142,0.0007438413,0.001495816,0.0001368057,0.0003619922,0.00005588076,0.001433298,0.0007244178,0.001391686],"category_scores_gemma":[0.0008109262,0.0005851364,0.0003283105,0.0005534284,0.0009168493,0.0003211599,0.000483992,0.002640583,0.00003371429],"about_ca_system_candidate":false,"about_ca_system_consensus":false,"about_ca_system_score_codex":0.0002445767,"about_ca_system_score_gemma":0.0006308684,"about_ca_topic_candidate":false,"about_ca_topic_consensus":false,"about_ca_topic_score_codex":0.0000725436,"about_ca_topic_score_gemma":0.00001468485,"domain_scores_codex":[0.9951676,0.001004171,0.001787899,0.0005162932,0.0006797098,0.0008443386],"domain_scores_gemma":[0.9925953,0.00329464,0.002060095,0.0006029977,0.0007106293,0.0007362974],"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":[0.004188085,0.0006706791,0.005283745,0.000157952,0.0011698,0.0000952051,0.002338798,0.0002327416,0.9794809,0.00003336785,0.00368207,0.002666676],"study_design_scores_gemma":[0.003899433,0.0006458022,0.0008470372,0.0002405117,0.001597538,0.001462271,0.001021412,0.0004259421,0.9753326,0.003308211,0.01053557,0.0006836455],"study_design_candidate":"bench_or_experimental","study_design_consensus":"bench_or_experimental","genre_codex":"empirical","genre_gemma":"empirical","genre_scores_codex":[0.9853306,0.008153769,0.0003176449,0.001476039,0.0009917322,0.0004294473,0.00021003,0.00006438509,0.003026381],"genre_scores_gemma":[0.9940736,0.001931152,0.0005390593,0.00119041,0.001646737,0.00001348892,0.00001235958,0.0001185459,0.0004746143],"genre_candidate":"empirical","genre_consensus":"empirical","teacher_disagreement_score":0.008743062,"threshold_uncertainty_score":0.9996604,"prediction_status":"machine_predicted_unvalidated"},"machine_scores":{"provisional":true,"baseline":true,"maturity_gate_passed":false,"score_opus":0.07936308988915702,"score_gpt":0.3732055936224697,"score_spread":0.2938425037333127,"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."}}