A convenient synthesis of new enantiomerically pure trihydroxypyrrolizidines using l-erythrose glycosylhydroxylamine as a masked acyclic chiral nitrone |
| |
Authors: | Nikolaos G Argyropoulos Petros Gkizis Evdoxia Coutouli-Argyropoulou |
| |
Institution: | Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece |
| |
Abstract: | A route has been developed for the synthesis of enantiomerically pure trihydroxylated pyrrolizidines starting from l-erythrose glycosylhydroxylamine. The latter acts as a masked acyclic nitrone and reacts diastereoselectively from its Re-face with methyl acrylate to give the corresponding isoxazolidines, which after reductive N-O cleavage are recyclized to trihydroxypyrrolizidines via a Mitsunobu condensation. |
| |
Keywords: | Trihydroxy pyrrolizidines Glycosylhydroxylamine Chiral nitrone Aza sugars Dipolar cycloaddition |
本文献已被 ScienceDirect 等数据库收录! |