title: Heck cyclization strategy for preparation of erythrinan alkaloids: asymmetric synthesis of unnatural (-)-erysotramidine from L-tartaric acid.
abstract: With an imide derived from L-tartaric acid as the starting material, ent-erysotramidine was synthesized for the first time. The synthesis features the use of the enantiopure synthon, prepared in a set of highly stereoselective reactions, including N-acyliminium cyclization, dihydrofuranyl ring formation via silver-catalyzed intramolecular alcohol addition to acetylene, and vinyl ether catalytic hydrogen reduction. The crucial step of the synthesis, assembly of ring A, was achieved by using Heck cyclization of (Z)-iodoolefin.
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences , Kasprzaka 44/52, 01-224 Warsaw, Poland.
authors.forename: Danuta
authors.initials: D
authors.lastname: Mostowicz
authors.forename: Mirosław
authors.initials: M
authors.lastname: Dygas
authors.forename: Zbigniew
authors.initials: Z
authors.lastname: Kałuża
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013644:Tartrates / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; D013644:Tartrates; C492626:erysotramidine; C007622:erythrinine