{"id":"W2428700530","doi":"10.1021/acs.orglett.5b01906","title":"Stereoselective and Regiodivergent Allylic Suzuki–Miyaura Cross-Coupling of 2-Ethoxydihydropyranyl Boronates: Synthesis and Confirmation of Absolute Stereochemistry of Diospongin B","year":2015,"lang":"en","type":"article","venue":"Organic Letters","topic":"Traditional and Medicinal Uses of Annonaceae","field":"Biochemistry, Genetics and Molecular Biology","cited_by":39,"is_retracted":false,"has_abstract":true,"ca_institutions":"University of Alberta","funders":"Natural Sciences and Engineering Research Council of Canada","keywords":"Chemistry; Dihydropyran; Enantioselective synthesis; Stereoselectivity; Allylic rearrangement; Stereochemistry; Natural product; Absolute configuration; Chiral ligand; Cycloaddition; Ligand (biochemistry); Aryl; Combinatorial chemistry; 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":"metacan-v3-hybrid-931329e0061c","candidate_categories":[],"consensus_categories":[],"category_scores_codex":[0.0002532928,0.0004762591,0.0002022511,0.00023954,0.0001954763,0.0002043424,0.0003196479,0.0002246589,0.0009009831],"category_scores_gemma":[0.0001428584,0.0001955581,0.000155455,0.0002348687,0.0002686065,0.0002321065,0.0002913748,0.0004638759,0.0004794535],"about_ca_system_candidate":false,"about_ca_system_consensus":false,"about_ca_system_score_codex":0.0003014412,"about_ca_system_score_gemma":0.0004280026,"about_ca_topic_candidate":false,"about_ca_topic_consensus":false,"about_ca_topic_score_codex":0.0009375187,"about_ca_topic_score_gemma":0.001882492,"domain_scores_codex":[0.9998497,0.0000312475,0.00001386363,0.00003156372,0.00003002943,0.00004359387],"domain_scores_gemma":[0.9999133,0.000008462339,0.00002279091,0.00001438941,0.0000114665,0.00002957223],"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":[0.00006785432,0.00001971275,0.00008480699,0.00004171853,0.000005516173,0.0001234594,0.00004682089,0.0001478519,0.9961356,0.0003604309,0.00004504946,0.002921306],"study_design_scores_gemma":[0.00001780275,0.0002229243,0.0006300813,0.000004091423,0.000007548373,0.0001368509,0.00002006678,0.0002677927,0.9959528,0.00008349031,0.002647675,0.000008769939],"study_design_candidate":"bench_or_experimental","study_design_consensus":"bench_or_experimental","genre_codex":"empirical","genre_gemma":"empirical","genre_scores_codex":[0.9649525,0.001779715,0.0216773,0.0001162745,0.00004508618,0.0001266566,0.0005532062,0.0001495031,0.01059978],"genre_scores_gemma":[0.9862269,0.001243883,0.009141614,0.00005089428,0.000008437956,0.00003370213,0.0003461947,0.00003022123,0.002918137],"genre_candidate":"empirical","genre_consensus":"empirical","teacher_disagreement_score":0.0009375187,"threshold_uncertainty_score":0.003014088,"prediction_status":"machine_predicted_unvalidated"},"machine_scores":{"provisional":true,"baseline":true,"maturity_gate_passed":false,"score_opus":0.0146258493434059,"score_gpt":0.2385920304412976,"score_spread":0.2239661810978917,"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."}}