Asymmetrized tris(hydroxymethyl)methane as a precursor of N- and O-containing 6-membered heterocycles through ring-closing metathesis.
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.
Banfi
Luca
L
Dipartimento di Chimica e Chimica Industriale, Via Dodecaneso 31, I-16146, Genova, Italy.
Guanti
Giuseppe
G
Paravidino
Monica
M
Riva
Renata
R
D003500:Cyclization; D006571:Heterocyclic Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry*
D006571:Heterocyclic Compounds; D008697:Methane