title: A Stereoselective Synthesis of Lentiginosine.
abstract: A concise stereoselective synthesis of (-)-lentiginosine, an iminosugar endowed with an interesting proapoptotic activity, has been accomplished using an enantiopure pyrroline N-oxide building block derived from d-tartaric acid. Key steps are a totally diastereoselective nucleophilic addition to the cyclic nitrone followed by a combination of two simultaneous and two tandem reactions occurring under the same conditions in a single laboratory operation. Natural (+)-lentiginosine can be synthesized by the same method but starting from l-tartaric acid.
authors.affiliation: Dipartimento di Chimica "Ugo Schiff", Università di Firenze , via della Lastruccia 13, 50019 Sesto Fiorentino (FI), Italy.
authors.forename: Franca M
authors.initials: FM
authors.lastname: Cordero
authors.affiliation: Dipartimento di Chimica "Ugo Schiff", Università di Firenze , via della Lastruccia 13, 50019 Sesto Fiorentino (FI), Italy.
authors.forename: Carolina
authors.initials: C
authors.lastname: Vurchio
authors.affiliation: Dipartimento di Chimica "Ugo Schiff", Università di Firenze , via della Lastruccia 13, 50019 Sesto Fiorentino (FI), Italy.
authors.forename: Alberto
authors.initials: A
authors.lastname: Brandi
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D050111:Imino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013644:Tartrates / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D050111:Imino Sugars; D013644:Tartrates; C063984:lentiginosine; C029768:tartaric acid