Highly stereocontrolled synthesis of the key intermediate of 1β-methylcarbapenem antibiotic via intramolecular nitrone 1,3-dipolar cycloaddition
Abstract
The key synthetic intermediate of 1β-methylcarbapenem antibiotic, (–)-(3S, 4R)-3-[(1R)-1-t- butyl-dimethylsiloxyethyl]-4-[(2R)-2-(1-hydroxypropyl)]azetidin-2-one (2), was synthesised from (R)-methyl 3-hydroxy-2-methylpropionate with high stereoselectivity via intramolecular nitrone 1,3-dipolar cycloaddition.