Syntheses of ficuseptine, juliprosine, and juliprosopine by biomimetic intramolecular Chichibabin pyridine syntheses.
[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.
Snider
Barry B
BB
Department of Chemistry MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA. snider@brandeis.edu
Neubert
Bobbianna J
BJ
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
D000470:Alkaloids; D007212:Indolizines; D010616:Phenanthrenes; D011725:Pyridines; C503000:ficuseptine B; C508951:juliprosine; C048175:juliflorine; C023666:pyridine