title: Formal enantioselective total synthesis of schulzeines A-C via Pd-catalyzed intramolecular asymmetric allylic amination.
abstract: Formal enantioselective total synthesis of schulzeines A-C was accomplished, featuring highly efficient Pd-catalyzed asymmetric allylic amination using novel diphosphonite ligands (BOPs) to provide 1-vinyltetrahydroisoquinoline key intermediates, as well as Ru-catalyzed ring-closing metathesis reaction to construct the key tricyclic cores in enantiopure form with correct absolute configurations.
authors.affiliation: Department of Chemistry, State University of New York at Stony Brook, Stony Brook, New York 11794-3400, USA.
authors.forename: Chi-Feng
authors.initials: CF
authors.lastname: Lin
authors.forename: Iwao
authors.initials: I
authors.lastname: Ojima
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D054837:Quinolizidines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013463:Sulfuric Acid Esters / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000498:Allyl Compounds; D006575:Heterocyclic Compounds, 3-Ring; D007769:Lactams; D008024:Ligands; D054837:Quinolizidines; D013463:Sulfuric Acid Esters; C541694:schulzeine A; C523671:schulzeine B; C523672:schulzeine C; D010165:Palladium