title: Synthesis of 1,2-dihydroxyindolizidines from 1-(2-pyridyl)-2-propen-1-ol.
abstract: 1-(2-Pyridyl)-2-propen-1-ol, obtained by vinylation of commercially available picolinaldehyde, resulted a good starting material for the synthesis of the indolizidine skeleton. In particular, a simple process involving bromination, reduction, and nucleophilic substitution (via elimination and addition) allowed an easy conversion of the starting material into (±)-lentiginosine in ~27% overall yield.
authors.affiliation: Dipartimento di Chimica Ugo Schiff, Università di Firenze, Polo Scientifico e Tecnologico, Sesto Fiorentino, Italy. donatella.giomi@unifi.it
authors.forename: Donatella
authors.initials: D
authors.lastname: Giomi
authors.forename: Renzo
authors.initials: R
authors.lastname: Alfini
authors.forename: Alessandra
authors.initials: A
authors.lastname: Micoli
authors.forename: Elisa
authors.initials: E
authors.lastname: Calamai
authors.forename: Cristina
authors.initials: C
authors.lastname: Faggi
authors.forename: Alberto
authors.initials: A
authors.lastname: Brandi
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C570130:1-(2-pyridyl)-2-propen-1-ol; D000470:Alkaloids; D020005:Propanols; D011725:Pyridines; C522921:picolinaldehyde; C063984:lentiginosine