A novel synthetic application of asymmetrized tris(hydroxymethyl)rnethane (THYM*) 1, obtained in both enantiomeric forms in high e.e. via a chemoenzymatic procedure, is described. Starting from the common precursor 3, 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 6 and 28 have been explored and, in the case of 28, conversion into the glycosidase inhibitor isofagomine 53 has been achieved.

Asymmetrized tris(hydroxymethyl)methane as precursor of N- and O-containing 6-membered heterocycles through ring-closing metathesis

BANFI, LUCA;GUANTI, GIUSEPPE;RIVA, RENATA
2005-01-01

Abstract

A novel synthetic application of asymmetrized tris(hydroxymethyl)rnethane (THYM*) 1, obtained in both enantiomeric forms in high e.e. via a chemoenzymatic procedure, is described. Starting from the common precursor 3, 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 6 and 28 have been explored and, in the case of 28, conversion into the glycosidase inhibitor isofagomine 53 has been achieved.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11567/246324
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