title: Syntheses of ficuseptine, juliprosine, and juliprosopine by biomimetic intramolecular Chichibabin pyridine syntheses.
abstract: [structure: see text] Biomimetic intramolecular Chichibabin pyridine syntheses using two molecules of an aldehyde and 4-aminobutanal dimethyl acetal (6) proceed efficiently in AcOH at 95 degrees C to give 2,3-dihydro-1H-indolizinium salts. Reaction occurs at 25 degrees C if 1-pyrroline (5) is used instead of 6. This reaction has been used for a one-step synthesis of ficuseptine (1) and the first syntheses of juliprosine (2) and juliprosopine (17t), which is now assigned as the trans stereoisomer.
authors.affiliation: Department of Chemistry MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA. snider@brandeis.edu
authors.forename: Barry B
authors.initials: BB
authors.lastname: Snider
authors.forename: Bobbianna J
authors.initials: BJ
authors.lastname: Neubert
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D007212:Indolizines / Q000138:chemical synthesis*; D015394:Molecular Structure; D010616:Phenanthrenes / Q000138:chemical synthesis*; D010946:Plants, Medicinal / Q000737:chemistry; D029862:Prosopis / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D007212:Indolizines; D010616:Phenanthrenes; D011725:Pyridines; C503000:ficuseptine B; C508951:juliprosine; C048175:juliflorine; C023666:pyridine