title: Asymmetrized tris(hydroxymethyl)methane as a precursor of N- and O-containing 6-membered heterocycles through ring-closing metathesis.
abstract: A novel synthetic application of asymmetrized tris(hydroxymethyl)methane (THYM), obtained in both enantiomeric forms in high e.e. via a chemoenzymatic procedure, is described. Starting from the common precursor , N- and O-containing 6-membered heterocycles have been prepared exploiting ring-closing metathesis as the key step. Possible elaborations of the double bond in and have been explored and, in the case of , conversion into the glycosidase inhibitor isofagomine has been achieved.
authors.affiliation: Dipartimento di Chimica e Chimica Industriale, Via Dodecaneso 31, I-16146, Genova, Italy.
authors.forename: Luca
authors.initials: L
authors.lastname: Banfi
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Guanti
authors.forename: Monica
authors.initials: M
authors.lastname: Paravidino
authors.forename: Renata
authors.initials: R
authors.lastname: Riva
mesh_terms: D003500:Cyclization; D006571:Heterocyclic Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry*
chemical_list: D006571:Heterocyclic Compounds; D008697:Methane