{"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":"codex-gemma-dda1882f352a","candidate_categories":[],"consensus_categories":[],"category_scores_codex":[0.0001730563,0.0001170923,0.0002077739,0.00003361729,0.00002048348,0.000005562309,0.000090229,0.00007985406,0.0000136095],"category_scores_gemma":[0.000109074,0.0001103332,0.00003937696,0.00005458496,0.0002716985,0.00001083773,0.00005147636,0.0000537423,4.237692e-7],"about_ca_system_candidate":false,"about_ca_system_consensus":false,"about_ca_system_score_codex":0.00001411538,"about_ca_system_score_gemma":0.00006028243,"about_ca_topic_candidate":false,"about_ca_topic_consensus":false,"about_ca_topic_score_codex":0.0000389393,"about_ca_topic_score_gemma":0.000004111249,"domain_scores_codex":[0.9992704,0.000009155362,0.0002526228,0.0001934001,0.0001570677,0.0001173649],"domain_scores_gemma":[0.9993992,0.0000386935,0.000196853,0.0001428032,0.0001431245,0.00007929179],"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":[0.000171578,0.00003445862,0.004064495,0.0001570827,0.0001013245,0.000001952202,0.0002585416,0.00002265617,0.9947198,0.0000241008,0.0003013973,0.000142611],"study_design_scores_gemma":[0.0006387798,0.000164964,0.0235294,0.00008074955,0.00005150424,0.00002725933,0.0002005674,0.00004611372,0.9749852,0.0000285634,0.0001371358,0.0001097266],"study_design_candidate":"bench_or_experimental","study_design_consensus":"bench_or_experimental","genre_codex":"empirical","genre_gemma":"empirical","genre_scores_codex":[0.998477,0.0007537802,0.000178329,0.0003654695,0.00004114578,0.000087443,0.00006073008,0.000004132994,0.00003198478],"genre_scores_gemma":[0.999406,0.0001826546,0.0001709165,0.0001260262,0.00004421287,0.000003376703,0.0000400987,0.000011224,0.00001543789],"genre_candidate":"empirical","genre_consensus":"empirical","teacher_disagreement_score":0.01973457,"threshold_uncertainty_score":0.4499256,"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."}}