title: Stereoselective total synthesis of the putative structure of nitraraine.
abstract: After the structure originally proposed for nitraraine was shown to be incorrect by total synthesis, the alternative structure 5 was recently suggested for the alkaloid on biosynthetic grounds and by comparison with the (1)H NMR data of tangutorine. The unambiguous synthesis of 5 is reported from tryptophanol and ketodiester 6, via oxazoloquinolone lactam 7. However, the melting point and (1)H NMR data of 5 did not match those reported for the natural product.
authors.affiliation: Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine (IBUB), University of Barcelona , 08028-Barcelona, Spain.
authors.forename: Federica
authors.initials: F
authors.lastname: Arioli
authors.forename: Maria
authors.initials: M
authors.lastname: Pérez
authors.forename: Fabiana
authors.initials: F
authors.lastname: Subrizi
authors.forename: Núria
authors.initials: N
authors.lastname: Llor
authors.forename: Joan
authors.initials: J
authors.lastname: Bosch
authors.forename: Mercedes
authors.initials: M
authors.lastname: Amat
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002243:Carbolines / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014364:Tryptophan / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D000470:Alkaloids; D001688:Biological Products; D002243:Carbolines; D004952:Esters; D026121:Indole Alkaloids; D007769:Lactams; D011807:Quinolizines; C000595172:nitraraine; C485396:tangutorine; C069544:tryptophanol; D014364:Tryptophan